CN102596968A - Insecticidal 4-amino-thieno[2,3-d]-pyrimidine compounds and methods of their use - Google Patents
Insecticidal 4-amino-thieno[2,3-d]-pyrimidine compounds and methods of their use Download PDFInfo
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- CN102596968A CN102596968A CN2010800405366A CN201080040536A CN102596968A CN 102596968 A CN102596968 A CN 102596968A CN 2010800405366 A CN2010800405366 A CN 2010800405366A CN 201080040536 A CN201080040536 A CN 201080040536A CN 102596968 A CN102596968 A CN 102596968A
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Insecticidal 4-Amino--thieno[2,3-d]-pyrimidine compounds and methods of their use to control pests that damage plants and crops and parasites that harm animals. The present invention relates to new insecticidal 4-Amino--thieno[2,3-d]-pyrimidine compounds and new methods of their use. The new 4-Amino--thieno[2,3-d]-pyrimidine derivatives have formula (I), wherein X, R1, R2, R3 and A are defined as in the description. The invention relates also to their enantiomer, diastereomer or agriculturally or veterinary acceptable salt thereof. The invention relates also to agricultural and veterinary compositions comprising such compounds. The invention relates further also to different insecticidal methods applying such compounds and compositions.
Description
The cross reference related application
The rights and interests of the right of priority of the U.S. Provisional Patent Application that the application requires to submit on July 30th, 2009 number 61/229,769 are all incorporated it into this paper by reference.
Invention field
The present invention relates to new desinsection and parasiticide 4-amino-thieno-[2,3-d]-pyrimidine compound, comprise said compound compositions, and new method of use.
Background of invention
Animal pest damages farm crop in the growth and that gathered in the crops and attacks wooden house and commercial building, causes the heavy economic losses of food supply and property.Though known a large amount of sterilant because target pest is directed against the ability that said sterilant development resistance, needs the novel agent of combating animal pests continuously.Particularly, animal pest such as insects and mite class are difficult to effectively prevent and kill off.
Thienopyrimidines is known and has been described in prior art.Mentioned the aralkylamine verivate of 4-amino-thienopyrimidines at EP-A 0370704 and US 5,141,941, and also described the fungicidal purposes of aralkylamine verivate among the EP 424125 as the tool bactericidal property.4-amino-Thienopyrimidine derivative compsn also has been described in DE-A 2654090 and US 4,146,716, is used to prevent and kill off fungi, virus and bacillary plant disease and insect damage.In EP-A 0452002, disclose N-through substituted-Thienopyrimidine-4-amine, it has fungicidal, kills insect and kills itch mite effectiveness.JP-A 2004-238380 has described the preparation of 4-phenylethyl aminopyrimidine and has been used as the purposes of sterilant.Thienopyrimidine compound with Fungicidally active has been described in WO 2006/047397 and US 2006/0089370A1 and WO2007/046809.Oxyalkylated 4-amino-thieno-[2,3-d]-pyrimidine compound has been described WO 2007/135029 and US 2009/0203524A1.The N-that has weeding, growth regulating and kill insect active has been described in EP-A 0447891 through substituted 4-amino-thieno-[2,3-d]-pyrimidine compound.The disclosure of by reference preceding text being quoted is all incorporated this paper separately into.
Any disclosed application that this paper is quoted and patent and wherein or whole documents of in its application process, quoting (" application citing document "); With quote or whole documents of mentioning and whole documents (" this paper citing document ") that this paper quotes or mention in the application of reference citation; Whole documents that quote or that mention in the document of quoting with this paper; And this paper or this paper any manufacturer's through quoting any product of mentioning in any document of incorporating into guide, explanation, product description and description of product page or leaf, incorporate this paper by reference into and can be used for embodiment of the present invention at this.
Among the application to any document to quote or indicate not be to admit that this kind document is a prior art of the present invention.
Although some tool kills the existing report of the thienopyrimidines of insect active, still need the desinsection of tool improvement and the compound of parasitocidal activity constantly, particularly resist the compound of mite class.
Therefore, theme of the present invention provides method and the compound with good insecticidal, particularly the antagonism insects that is difficult to prevent and kill off and the method and the compound of mite class.
Brief summary of the invention
Found that theme of the present invention is able to solve through 4-amino-thieno-[2, the 3-d]-pyrimidine derivatives of new general formula I:
Variable X wherein, A, R
1, R
2And R
3Be described below, or the acceptable salt of its pharmacy.In one embodiment, the present invention provides agricultural and veterinary compositions, and it comprises at least a formula I compound or its enantiomorph, diastereomer or the salt of significant quantity, and agricultural goes up acceptable or veterinary science acceptable carrier.
In another embodiment, the present invention provides agricultural or veterinary compositions, it comprises at least a formula I compound, and other desinsection or parasitocidal activity reagent are gone up acceptable or veterinary science acceptable carrier with agricultural.
In another embodiment; The present invention provides with formula I compound or comprises method and the purposes that animal pest, protection farm crop or protective plant reproductive material were resisted or prevented and kill off to said compound compositions; Comprise farm crop; Plant propagation material or animal pest, their habitat, breeding farm; Food supply, plant, seed, soil, zone, material or environment that the growth of wherein said animal pest maybe can be grown, perhaps the desire protection is in order to avoid animal pest is attacked or material, plant, seed, soil, surface or the space of infecting contact with at least a formula I compound or its enantiomorph, diastereomer or the salt of insecticidal effective dose.
The present invention also provides in the antagonism animal body or ectozoal method and purposes; Handle, prevent and kill off or prevent the parsitism on the animal or method that infects and purposes; Comprise at least a formula I compound of parasiticide significant quantity or comprise this compound compositions; Or the acceptable salt of its enantiomorph, diastereomer or veterinary science, be applied to animal.
It should be noted that in the disclosure and especially in claim and/or paragraph, term can have united states patent law like " comprising ", " comprising ", " containing " etc. and give its implication; For example, they can mean " comprising ", " containing ", " comprising " etc.; And term as " basically by ... form " have united states patent law with " basically by ... composition " and give its implication; For example; Their allow the element clearly do not described, but get rid of find in the prior art or influence the present invention basically or the element of new feature.
These with other embodiment by following detailed description part disclosed or instruct and contain.
Detailed Description Of The Invention
The present invention provides 4-amino-thieno-new and creationary general formula I [2,3-d] pyrimidine derivatives:
Wherein
X is selected from halogen, C
1-C
10-alkyl or C
1-C
10-alkylhalide group;
R
1Be selected from down group: hydrogen, halogen, formyl radical, C
1-C
10-alkyl, C
1-C
10-thiazolinyl, C
1-C
10Alkynyl, C
1-C
10-alkylhalide group, C
1-C
10-haloalkenyl, C
1-C
10-alkynyl halide, C
1-C
10-alkoxyl group, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
10-halogen alkoxyl group, C
1-C
10-alkylthio, C
1-C
10-alkyl halide sulfenyl, C
1-C
10-alkane sulfinyl, C
1-C
10-alkyl halide sulfinyl, C
1-C
10-alkane alkylsulfonyl, C
1-C
10-alkylhalide group-alkylsulfonyl, C
1-C
10-alkylamino, C
1-C
10-alkyl halide is amino, two (C
1-C
10-alkyl) amino, two (C
1-C
10)-alkyl halide is amino, CN ,-CR
3=NOH ,-CR
3=NOCH
3With-CR
3=NOC
2H
5
R
2Be selected from down group: hydrogen, halogen, C
1-C
10-alkyl, C
1-C
10-alkylhalide group, C
1-C
10-alkoxyl group, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
10-halogen alkoxyl group, C
1-C
10-alkylthio, C
1-C
10-alkyl halide sulfenyl, C
1-C
10-alkane sulfinyl, C
1-C
10-alkyl halide sulfinyl, C
1-C
10-alkane alkylsulfonyl, C
1-C
10-alkylhalide group-alkylsulfonyl, C
1-C
10-alkylamino, C
1-C
10-alkyl halide is amino, two (C
1-C
10-alkyl) amino and two (C
1-C
10)-alkyl halide is amino;
R
3Be selected from hydrogen, C
1-C
10-alkyl or C
1-C
10-alkylhalide group;
A is
Wherein
N is 0,1 or 2;
R
4, R
5, R
8And R
9Be selected from hydrogen independently of each other, CN, C
1-C
10-alkyl or C
1-C
10-alkylhalide group;
R
6Be selected from down group: C
1-C
10The fluorine alkylhalide group, C
2-C
10The fluorine haloalkenyl, C
2-C
10Fluorine alkynyl halide and C
3-C
7Fluorine halogen naphthenic base, the carbon atom of wherein aforementioned fluorine alkylhalide group residue can further be used C
1-C
10-alkoxyl group, C
1-C
10-halogen alkoxyl group, cyanic acid and (C=O) R
qReplace, and wherein
R
qBe selected from down group: amino, C
1-C
6-alkoxyl group, C
1-C
6-halogen alkoxyl group, C
1-C
6-alkylamino, C
1-C
6-alkyl halide is amino, two (C
1-C
6-alkyl) amino and two (C
1-C
6)-alkyl halide is amino;
R
7Be selected from down group: hydrogen, halogen, CN, C
1-C
10-alkyl, C
1-C
10-alkylhalide group, C
1-C
10-alkoxyl group, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
10-halogen alkoxyl group, C
1-C
10-alkylthio and C
1-C
10-alkyl halide sulfenyl;
And/or its enantiomorph, diastereomer or agricultural go up or veterinarily acceptable salt at least.
Depend on the replacement form, compound according to the invention can comprise one or more chiral centres, and they exist as enantiomorph or non-enantiomer mixture in the case.The compsn that contains these mixtures be not only in theme of the present invention, and be to contain those of pure enantiomer or diastereomer.
Compound according to the invention can also exist with the crystals with different modification that is used for purposes of the present invention, and can have different biological activitys.These crystals with different modification also are themes of the present invention.
In addition, compound of the present invention can be used as hydrate or solvate exists, and wherein the water or the solvent of the amount of particular chemical metering combine with molecule in crystal formation.The hydrate of formula I compound and solvate also are themes of the present invention.
The present invention relates to use this kind compound and kill insect and parasiticidal method, and comprise following embodiment:
-agricultural and veterinary compositions, it comprises a certain amount of at least a formula I compound or its enantiomorph, diastereomer or salt;
-formula I compound or its enantiomorph, diastereomer or salt are used for antagonism or prevent and kill off animal pest;
-methods for combating animal pests; It comprises animal pest, their habitats, breeding farm; Food supply, plant, seed, soil, zone, material or environment that wherein said animal pest is being grown and maybe can grown, perhaps desire protection is in order to avoid animal pest is attacked or material, plant, seed, soil, surface or the space of infecting contact with at least a formula I compound or its enantiomorph, diastereomer or the salt of insecticidal effective dose;
-protection farm crop avoid the method that animal pest is attacked or infected, and it comprises farm crop are contacted with at least a formula I compound or its enantiomorph, diastereomer or the salt of insecticidal effective dose;
-protective plant reproductive material particularly seed avoids the method that soil insect class invasion and attack and protection seedling root and shoot avoid soil and the invasion and attack of blade face insects, be included in sow before and/or after vernalization with plant propagation material particularly seed contact with at least a formula I compound or its enantiomer, diastereomer or salt;
-contain the seed of formula I compound or its enantiomorph, diastereomer or salt;
-Shi I compound or the acceptable salt of its enantiomer, diastereomer or veterinary science are used to resist in the animal body and ectozoal purposes;
-Shi I compound or the acceptable salt of its enantiomer, diastereomer or veterinary science are in preparation antagonism animal body and the purposes of ectozoal medicine;
-be used to handle, prevent and kill off, prevent or watch for animals resist the method for parasite infestation or infection; It comprises that per os, part or parenteral use or give formula I compound or its enantiomer of parasiticide significant quantity, the acceptable salt of diastereomer and/or veterinary science to animal;
-preparation is used to handle, prevent and kill off, prevent or watches for animals resist the method for compositions of parasite infestation or infection, and it comprises formula I compound or its enantiomer of parasiticide significant quantity, the acceptable salt of diastereomer and/or veterinary science.
Be disclosed in WO 2006/047397 and comprise without substituent those compounds of substituted alkylthio and compare; Insect active is better killed in the substituted 4-amino-thieno-of the halogenated alkylthio of fluorine of the present invention [2,3-d]-pyrimidine compound demonstration astoundingly.They also show than WO 2007/135029 oxyalkylated 4-amino-thieno-[2,3-d]-pyrimidine compound better renders a service.
Formula I compound and agricultural thereof go up or the acceptable salt high reactivity of veterinary science ground combating animal pests, and promptly harmful arthropod and threadworms are particularly resisted insects and the mite class that is difficult to prevent and kill off.
In addition, the salt of formula I compound is preferably agriculture goes up or the acceptable salt of veterinary science.They can be formed in the ordinary method, for example, if formula I compound have alkaline official can through compound is reacted with relevant anionic acid, perhaps the acd compound of formula I and suitable alkali are reacted.
Useful salt is those cationic salt or those sour acid salt particularly, and its positively charged ion and negatively charged ion do not have any unfavorable effect to the effect of compound according to the present invention respectively.Suitable positively charged ion is the ion of alkali metal preferred, lithium, sodium and potassium particularly, the ion of the example of the preferred calcium of earth alkali metal, magnesium and barium and the preferred manganese of transition metal, copper, zinc and iron, and ammonium (NH
4 +) with through substituted ammonium, wherein in the Wasserstoffatoms one to four use C
1-C
4-alkyl, C
1-C
4-hydroxyalkyl, C
1-C
4-alkoxyl group, C
1-C
4-alkoxy-C
1-C
4-alkyl, hydroxyl-C
1-C
4-alkoxy-C
1-C
4-alkyl, phenyl or benzyl replacement.Instance through substituted ammonium ion comprises ammonium methyl, sec.-propyl ammonium, Dimethyl Ammonium, di-isopropyl ammonium; Trimethyl ammonium, tetramethyl-ammonium, tetraethyl ammonium, TBuA; 2-hydroxyethyl ammonium, 2-(2-hydroxyl-oxethyl) ethyl-ammonium, two (2-hydroxyethyl) ammonium, benzyltrimethylammon.um and benzyl triethyl ammonium ammonium; And phosphonium ion, sulfonium cation, preferred three (C
1-C
4-alkyl) sulfonium and sulfoxonium ion, preferred three (C
1-C
4-alkyl) sulfoxonium.
The negatively charged ion of useful acid salt mainly is a cl anion, bromine anions, fluorine anion, hydrosulphuric acid negatively charged ion; Sulfate anion, dihydrogen phosphoric acid negatively charged ion, hydrogen phosphate anion, phosphate anion; The nitric acid negatively charged ion, bicarbonate anion, carbonate anion, hexafluorosilicic acid negatively charged ion; The phosphofluoric acid negatively charged ion, phenylformic acid negatively charged ion, and C
1-C
4-paraffinic acid negatively charged ion, preferable formic acid negatively charged ion, acetate negatively charged ion, propionic acid negatively charged ion and butyric acid negatively charged ion.They can be through forming the preferred hydrochloric acid of the acid of formula I compound and respective anionic, Hydrogen bromide, sulfuric acid, phosphoric acid or nitric acid reaction.
Term used herein has their conventional sense in the art, only if appointment is arranged in addition.In the definition of above-mentioned formula I, said substituting group has following implication:
The organic moiety of in above variable-definition, mentioning is, such as term halogen, and the collective term of group member's independent tabulation separately.Prefix C
n-C
mUnder each situation, refer to possible carbonatoms in the said group.
Term halogen is represented fluorine, bromine, chlorine or iodine under each situation.In one embodiment of the invention, halogen is a fluorine or chlorine.
Term " C
1-C
10-alkyl " moieties as used herein and alkylamino and dialkyl amido is meant and comprises that those have 1 to 10 carbon atom respectively, 1 to 6 carbon atom and the saturated straight chain of 1 to 4 carbon-based group or the hydrocarbyl group of branching.C
1-C
10The instance of alkyl includes but not limited to, methyl, ethyl, propyl group, 1-methylethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1; The 1-dimethyl ethyl, amyl group, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethyl propyl, 1-ethyl propyl, hexyl; 1,1-dimethyl propyl, 1,2-dimethyl propyl, 1-methyl amyl, 2-methyl amyl, 3-methyl amyl, 4-methyl amyl, 1; The 1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl; 3,3-dimethylbutyl, 1-ethyl-butyl, 2-ethyl-butyl, 1,1,2-trimethylammonium propyl group, 1; 2,2-trimethylammonium propyl group, 1-ethyl-1-methyl-propyl, 1-ethyl-2-methyl-propyl, heptyl, octyl group, 2-ethylhexyl, nonyl and decyl and isomer thereof.C
1-C
4-alkyl means for example methyl, ethyl, propyl group, 1-methylethyl, butyl, 1-methyl-propyl, 2-methyl-propyl or 1,1-dimethyl ethyl.
Term " C
1-C
10-alkylhalide group " the straight chain with 1 to 10 carbon atom or the saturated alkyl group (as mentioned above) of branching of being meant as used herein, wherein some or all in the Wasserstoffatoms in these groups can be used halogen atom replacement as mentioned above.C for example
1-C
4-alkylhalide group includes, but not limited to chloromethyl, brooethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl; Trifluoromethyl, chlorine methyl fluoride, dichlorofluoromethyl, chlorodifluoramethyl-, 1-chloroethyl, 1-bromotrifluoromethane, 1-fluoro ethyl, 2-fluoro ethyl; 2,2-two fluoro ethyls, 2,2,2-trifluoroethyl, 2-chloro-2-fluoro ethyl, 2-chloro-2; 2-two fluoro ethyls, 2,2-two chloro-2-fluoro ethyls, 2,2,2-three chloroethyls, pentafluoroethyl group etc.
Term " C
1-C
2-fluoroalkyl " C that carries 1,2,3,4 or 5 fluorine atoms that is meant as used herein
1-C
2-alkyl, difluoromethyl for example, trifluoromethyl, 1-fluoro ethyl, 2-fluoro ethyl, 2,2-two fluoro ethyls, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoro ethyl or pentafluoroethyl group.
Term " C
1-C
10-fluorine alkylhalide group " the straight chain with 1 to 10 carbon atom or the saturated alkyl group (as mentioned above) of branching of being meant as used herein; it carries at least one fluorine atom, and wherein some or all in the residual hydrogen atom in these groups can be with the halogen atom replacement that independently is selected from fluorine, bromine, chlorine or iodine.
Term " C
1-C
10-alkoxyl group " the straight chain with 1 to 10 carbon atom or the saturated alkyl group (as mentioned above) of branching of being meant as used herein, it connects through Sauerstoffatom.Instance comprises C
1-C
6-alkoxyl group, like methoxyl group, oxyethyl group, OCH
2-C
2H
5, OCH (CH
3)
2, n-butoxy, OCH (CH
3)-C
2H
5, OCH
2-CH (CH
3)
2, OC (CH
3)
3, n-pentyloxy, 1-methyl butoxy, 2-methyl butoxy, 3-methyl butoxy, 1,1-dimethyl-propoxy-, 1; 2-dimethyl-propoxy-, 2,2-dimethyl--propoxy-, 1-ethyl propoxy-, n-hexyloxy, 1-methyl pentyloxy, 2-methyl pentyloxy, 3-methyl pentyloxy; 4-methyl pentyloxy, 1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy, 2; 2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy, 1-ethyl butoxy, 2-ethyl butoxy, 1; 1,2-trimethylammonium propoxy-, 1,2,2-trimethylammonium propoxy-, 1-ethyl-1-methyl propoxy-, 1-ethyl-2-methyl propoxy-etc.
Term " C
1-C
10-halogen alkoxyl group " as used hereinly be meant C as mentioned above
1-C
10-alkoxy base, it partially or completely replaces with fluorine, chlorine, bromine and/or iodine, i.e. C for example
1-C
6-halogen alkoxyl group, like the chlorine methoxyl group, dichloro methoxyl group, trichlorine methoxyl group, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group, dichloro fluorine methoxyl group; The chloro difluoro-methoxy, 2-fluorine oxyethyl group, 2-chloroethoxy, 2-bromine oxethyl, 2-iodine oxyethyl group, 2,2-difluoroethoxy, 2,2; The 2-trifluoro ethoxy, 2-chloro-2-fluorine oxyethyl group, 2-chloro-2,2-difluoroethoxy, 2,2-two chloro-2-fluorine oxyethyl groups, 2,2; 2-three chloroethoxies, five fluorine oxyethyl groups, 2-fluorine propoxy-, 3-fluorine propoxy-, 2,2-difluoro propoxy-, 2,3-difluoro propoxy-; 2-chlorine propoxy-, 3-chlorine propoxy-, 2,3-dichloro propoxy-, 2-bromine propoxy-, 3-bromine propoxy-, 3,3; 3-trifluoro propoxy-, 3,3,3-trichlorine propoxy-, 2,2,3,3; 3-five fluorine propoxy-, seven fluorine propoxy-, 1-(methyl fluoride)-2-fluorine oxyethyl group, 1-(chloromethyl)-2-chloroethoxy, 1-(brooethyl)-2-bromine oxethyl, 4-fluorine butoxy, 4-chlorine butoxy, 4-bromine butoxy; Nine fluorine butoxy, 5-fluoro-1-pentyloxy, 5-chloro-1-pentyloxy, 5-bromo-1-pentyloxy, 5-iodo-1-pentyloxy, 5,5,5-three chloro-1-pentyloxys; 11 fluorine pentyloxys, 6-fluoro-1-hexyloxy, 6-chloro-1-hexyloxy, 6-bromo-1-hexyloxy, 6-iodo-1-hexyloxy, 6,6,6-three chloro-1-hexyloxy or ten difluoro hexyloxy.In one embodiment of the invention, " C
1-C
10-halogen alkoxyl group " be selected from down group: chlorine methoxyl group, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, 2-fluorine oxyethyl group, 2-chloroethoxy and 2,2,2-trifluoro ethoxy.
Term " C
1-C
6-alkoxy-C
1-C
6-alkyl " as used herein being meant through C as mentioned above
1-C
6The substituted C of-alkoxyl group
1-C
6-alkyl, promptly for example, CH
2-OCH
3, CH
2-OC
2H
5, n-propoxy-methyl, CH
2-OCH (CH
3)
2, n-butoxymethyl, (1-methyl propoxy-) methyl, (2-methyl propoxy-) methyl, CH
2-OC (CH
3)
3, 2-(methoxyl group) ethyl, 2-(oxyethyl group) ethyl, 2-(n-propoxy-) ethyl, 2-(1-methyl ethoxy) ethyl; 2-(n-butoxy) ethyl, 2-(1-methyl propoxy-) ethyl, 2-(2-methyl propoxy-) ethyl, 2-(1,1-dimethyl-oxyethyl group) ethyl; 2-(methoxyl group) propyl group, 2-(oxyethyl group) propyl group, 2-(n-propoxy-) propyl group, 2-(1-methyl ethoxy) propyl group, 2-(n-butoxy) propyl group; 2-(1-methyl propoxy-) propyl group, 2-(2-methyl propoxy-) propyl group, 2-(1,1-dimethyl-oxyethyl group) propyl group, 3-(methoxyl group) propyl group; 3-(oxyethyl group) propyl group, 3-(n-propoxy-) propyl group, 3-(1-methyl ethoxy) propyl group, 3-(n-butoxy) propyl group, 3-(1-methyl propoxy-) propyl group; 3-(2-methyl propoxy-) propyl group, 3-(1,1-dimethyl-oxyethyl group) propyl group, 2-(methoxyl group) butyl, 2-(oxyethyl group) butyl; 2-(n-propoxy-) butyl, 2-(1-methyl ethoxy) butyl, 2-(n-butoxy) butyl, 2-(1-methyl propoxy-) butyl, 2-(2-methyl propoxy-) butyl; 2-(1,1-dimethyl-oxyethyl group) butyl, 3-(methoxyl group) butyl, 3-(oxyethyl group) butyl, 3-(n-propoxy-) butyl; 3-(1-methyl ethoxy) butyl, 3-(n-butoxy) butyl, 3-(1-methyl propoxy-) butyl, 3-(2-methyl propoxy-) butyl, 3-(1; 1-dimethyl-oxyethyl group) butyl, 4-(methoxyl group) butyl, 4-(oxyethyl group) butyl, 4-(n-propoxy-) butyl, 4-(1-methyl ethoxy) butyl; 4-(n-butoxy) butyl, 4-(1-methyl propoxy-) butyl, 4-(2-methyl propoxy-) butyl, 4-(1,1-dimethyl-oxyethyl group) butyl etc.
Term " C
1-C
6-alkoxy-C
1-C
6-alkoxyl group " as used herein being meant through C as mentioned above
1-C
6The substituted C of-alkoxyl group
1-C
6-alkoxyl group, promptly for example, OCH
2-OCH
3, OCH
2-OC
2H
5, n-propoxy-methoxyl group, OCH
2-OCH (CH
3)
2, n-butoxy methoxyl group, (1-methyl propoxy-) methoxyl group, (2-methyl propoxy-) methoxyl group, OCH
2-OC (CH
3)
3, 2-(methoxyl group) oxyethyl group, 2-(oxyethyl group) oxyethyl group, 2-(n-propoxy-) oxyethyl group, 2-(1-methyl ethoxy) oxyethyl group; 2-(n-butoxy) oxyethyl group, 2-(1-methyl propoxy-) oxyethyl group, 2-(2-methyl propoxy-) oxyethyl group, 2-(1,1-dimethyl-oxyethyl group) oxyethyl group; 2-(methoxyl group) propoxy-, 2-(oxyethyl group) propoxy-, 2-(n-propoxy-) propoxy-, 2-(1-methyl ethoxy) propoxy-, 2-(n-butoxy) propoxy-; 2-(1-methyl propoxy-) propoxy-, 2-(2-methyl propoxy-) propoxy-, 2-(1,1-dimethyl-oxyethyl group) propoxy-, 3-(methoxyl group) propoxy-; 3-(oxyethyl group) propoxy-, 3-(n-propoxy-) propoxy-, 3-(1-methyl ethoxy) propoxy-, 3-(n-butoxy) propoxy-, 3-(1-methyl propoxy-) propoxy-; 3-(2-methyl propoxy-) propoxy-, 3-(1,1-dimethyl-oxyethyl group) propoxy-, 2-(methoxyl group) butoxy, 2-(oxyethyl group) butoxy; 2-(n-propoxy-) butoxy, 2-(1-methyl ethoxy) butoxy, 2-(n-butoxy) butoxy, 2-(1-methyl propoxy-) butoxy, 2-(2-methyl propoxy-) butoxy; 2-(1,1-dimethyl-oxyethyl group) butoxy, 3-(methoxyl group) butoxy, 3-(oxyethyl group) butoxy; 3-(n-propoxy-) butoxy, 3-(1-methyl ethoxy) butoxy, 3-(n-butoxy) butoxy, 3-(1-methyl propoxy-) butoxy; 3-(2-methyl propoxy-) butoxy, 3-(1,1-dimethyl-oxyethyl group) butoxy, 4-(methoxyl group) butoxy; 4-(oxyethyl group) butoxy, 4-(n-propoxy-) butoxy, 4-(1-methyl ethoxy) butoxy, 4-(n-butoxy) butoxy; 4-(1-methyl propoxy-) butoxy, 4-(2-methyl propoxy-) butoxy, 4-(1,1-dimethyl-oxyethyl group) butoxy etc.
Term " C
1-C
4-alkoxy-C
1-C
4-alkoxy-C
1-C
4-alkoxyl group " as used herein being meant through C as mentioned above
1-C
4-alkoxy-C
1-C
4The substituted C of-alkoxyl group
1-C
4-alkoxyl group, promptly for example, 2-(2-methoxy ethyl oxygen base) ethyl oxygen base, 2-(2-ethoxyethyl group oxygen base) ethyl oxygen base.
Term " C
1-C
10-alkyl-carbonyl " the straight chain with 1 to 10 carbon atom (as mentioned above) or the saturated alkyl group of branching of being meant as used herein, it is via the carbon atom bonding of the carbonyl group at any key place in alkyl group.Instance comprises C
1-C
6-alkyl-carbonyl such as CO-CH
3, CO-C
2H
5, the n-propyl carbonyl, 1-methylethyl carbonyl, just-and the butyl carbonyl, 1-methyl-propyl carbonyl, 2-methyl-propyl carbonyl, 1; 1-dimethyl ethyl carbonyl, just-the amyl group carbonyl, 1-methylbutyl carbonyl, 2-methylbutyl carbonyl, 3-methylbutyl carbonyl, 1,1-dimethyl propyl carbonyl; 1,2-dimethyl propyl carbonyl, 2,2-dimethyl propyl carbonyl, 1-ethyl propyl carbonyl, just-and the hexyl carbonyl, 1-methyl amyl carbonyl; 2-methyl amyl carbonyl, 3-methyl amyl carbonyl, 4-methyl amyl carbonyl, 1,1-dimethylbutyl carbonyl, 1; 2-dimethylbutyl carbonyl, 1,3-dimethylbutyl carbonyl, 2,2-dimethylbutyl carbonyl, 2; 3-dimethylbutyl carbonyl, 3,3-dimethylbutyl carbonyl, 1-ethyl-butyl carbonyl, 2-ethyl-butyl carbonyl, 1; 1,2-trimethylammonium propyl group carbonyl, 1,2,2-trimethylammonium propyl group carbonyl, 1-ethyl-1-methyl-propyl carbonyl or 1-ethyl-2-methyl-propyl carbonyl etc.
Term " C
1-C
10-carbalkoxy " the straight chain with 1 to 10 carbon atom or the alkoxy base (as mentioned above) of branching of being meant as used herein, its carbon atom through carbonyl group connects.Instance comprises (C
1-C
6-alkoxyl group) carbonyl, for example CO-OCH
3, CO-OC
2H
5, COO-CH
2-C
2H
5, CO-OCH (CH
3)
2, n-butoxy carbonyl, CO-OCH (CH
3)-C
2H
5, CO-OCH
2-CH (CH
3)
2, CO-OC (CH
3)
3, n-pentyloxy carbonyl, 1-methyl butoxy carbonyl, 2-methyl butoxy carbonyl, 3-methyl butoxy carbonyl, 2,2-dimethyl-propoxycarbonyl; 1-ethyl propoxycarbonyl, n-hexyloxy carbonyl, 1,1-dimethyl-propoxycarbonyl, 1,2-dimethyl-propoxycarbonyl, 1-methyl pentyloxy carbonyl; 2-methyl pentyloxy carbonyl, 3-methyl pentyloxy carbonyl, 4-methyl pentyloxy carbonyl, 1,1-dimethyl-butoxy carbonyl, 1; 2-dimethyl-butoxy carbonyl, 1,3-dimethyl-butoxy carbonyl, 2,2-dimethyl-butoxy carbonyl, 2; 3-dimethyl-butoxy carbonyl, 3,3-dimethyl-butoxy carbonyl, 1-ethyl butoxy carbonyl, 2-ethyl butoxy carbonyl, 1; 1,2-trimethylammonium propoxycarbonyl, 1,2,2-trimethylammonium propoxycarbonyl, 1-ethyl-1-methyl propoxycarbonyl or 1-ethyl-2-methyl propoxycarbonyl.
Term " C
1-C
10-alkylthio (C
1-C
10-alkylsulfanyl:C
1-C
10-alkyl-S-) " the straight chain with 1 to 10 carbon atom or the saturated alkyl group (as mentioned above) of branching of being meant as used herein, it connects through sulphur atom, for example C
1-C
4-alkylthio such as methylthio group, ethylenebis dithiocarbamate, propyl dithiocarbamate, 1-methylethyl sulfo-, butyl sulfo-, 1-methyl-propyl sulfo-, 2-methyl-propyl sulfo-or 1,1-dimethyl ethyl sulfo-.
Term " C
1-C
10-alkane sulfinyl " (C
1-C
10-alkyl-S (=O)-), the straight chain with 1 to 10 carbon atom or the saturated hydrocarbyl group (as mentioned above) of branching of being meant as used herein, it is through sulphur atom link of the sulfinyl group at any key place in the alkyl group.Instance comprises C
1-C
6-alkane sulfinyl: SO-CH
3, SO-C
2H
5, the n-propyl sulfinyl, 1-methylethyl sulfinyl, just-and the butyl sulfinyl, 1-methyl-propyl sulfinyl, 2-methyl-propyl sulfinyl; 1,1-dimethyl ethyl sulfinyl, just-and the amyl group sulfinyl, 1-methylbutyl sulfinyl, 2-methylbutyl sulfinyl, 3-methylbutyl sulfinyl; 1,1-dimethyl propyl sulfinyl, 1,2-dimethyl propyl sulfinyl, 2,2-dimethyl propyl sulfinyl; 1-ethyl propyl sulfinyl, just-the hexyl sulfinyl, 1-methyl amyl sulfinyl, 2-methyl amyl sulfinyl, 3-methyl amyl sulfinyl, 4-methyl amyl sulfinyl; 1,1-dimethylbutyl sulfinyl, 1,2-dimethylbutyl sulfinyl, 1,3-dimethylbutyl sulfinyl; 2,2-dimethylbutyl sulfinyl, 2,3-dimethylbutyl sulfinyl, 3; 3-dimethylbutyl sulfinyl, 1-ethyl-butyl sulfinyl, 2-ethyl-butyl sulfinyl, 1,1; 2-trimethylammonium propyl group sulfinyl, 1,2,2-trimethylammonium propyl group sulfinyl, 1-ethyl-1-methyl-propyl sulfinyl or 1-ethyl-2-methyl-propyl sulfinyl.
Term " C
1-C
10-alkane alkylsulfonyl " (C
1-C
10-alkyl-S (=O)
2-) the straight chain with 1 to 10 carbon atom or the saturated alkyl group (as mentioned above) of branching of being meant as used herein, it is via the sulfur atom linkage of the alkylsulfonyl group at any key place in the alkyl group.Instance comprises C
1-C
6-alkane alkylsulfonyl such as SO
2-CH
3, SO
2-C
2H
5, n-propyl alkylsulfonyl, SO
2-CH (CH
3)
2, just-and the butyl alkylsulfonyl, 1-methyl-propyl alkylsulfonyl, 2-methyl-propyl alkylsulfonyl, SO
2-C (CH
3)
3, just-and the amyl group alkylsulfonyl, 1-methylbutyl alkylsulfonyl, 2-methylbutyl alkylsulfonyl, 3-methylbutyl alkylsulfonyl, 1,1-dimethyl propyl alkylsulfonyl; 1,2-dimethyl propyl alkylsulfonyl, 2,2-dimethyl propyl alkylsulfonyl, 1-ethyl propyl alkylsulfonyl, just-and the hexyl alkylsulfonyl, 1-methyl amyl alkylsulfonyl; 2-methyl amyl alkylsulfonyl, 3-methyl amyl alkylsulfonyl, 4-methyl amyl alkylsulfonyl, 1,1-dimethylbutyl alkylsulfonyl, 1; 2-dimethylbutyl alkylsulfonyl, 1,3-dimethylbutyl alkylsulfonyl, 2,2-dimethylbutyl alkylsulfonyl, 2; 3-dimethylbutyl alkylsulfonyl, 3,3-dimethylbutyl alkylsulfonyl, 1-ethyl-butyl alkylsulfonyl, 2-ethyl-butyl alkylsulfonyl, 1; 1,2-trimethylammonium sulfonyl propyl base, 1,2,2-trimethylammonium sulfonyl propyl base, 1-ethyl-1-methyl-propyl alkylsulfonyl or 1-ethyl-2-methyl-propyl alkylsulfonyl etc.
Term " C
2-C
10-thiazolinyl " straight chain of at least one two key or the undersaturated hydrocarbyl group of branching of being meant as used herein with 2 to 10 carbon atoms and optional position." C
2-C
10-thiazolinyl " group can comprise in chain more than a two key.Instance includes but not limited to, vinyl, 1-propenyl, 2-propenyl, 1-methyl-vinyl, 1-butylene base, crotyl, 3-crotonyl, 1-methyl isophthalic acid-propenyl, 2-methyl isophthalic acid-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; The 1-pentenyl, pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl isophthalic acid-crotonyl, 2-methyl-1-butene thiazolinyl, 3-methyl-1-butene base; 1-methyl-2-butene base, 2-methyl-2-butene base, 3-methyl-2-butene base, 1-methyl-3-crotonyl, 2-methyl-3-crotonyl, 3-methyl-3-crotonyl, 1; 1-dimethyl--2-propenyl, 1,2-dimethyl--1-propenyl, 1,2-dimethyl--2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl; The 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentene thiazolinyl, 2-methyl-1-pentene thiazolinyl; 3-methyl-1-pentene thiazolinyl, 4-methyl-1-pentene base, 1-methyl-pentenyl, 2-methyl-pentenyl, 3-methyl-pentenyl, 4-methyl-pentenyl, 1-methyl-3-pentenyl; 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl; 1,1-dimethyl--crotyl, 1,1-dimethyl--3-crotonyl, 1,2-dimethyl--1-butylene base, 1; 2-dimethyl--crotyl, 1,2-dimethyl--3-crotonyl, 1,3-dimethyl--1-butylene base, 1,3-dimethyl--crotyl; 1,3-dimethyl--3-crotonyl, 2,2-dimethyl--3-crotonyl, 2,3-dimethyl--1-butylene base, 2; 3-dimethyl--crotyl, 2,3-dimethyl--3-crotonyl, 3,3-dimethyl--1-butylene base, 3; 3-dimethyl--crotyl, 1-ethyl-1-butylene base, 1-ethyl-crotyl, 1-ethyl-3-crotonyl, 2-ethyl-1-butylene base, 2-ethyl-crotyl; 2-ethyl-3-crotonyl, 1,1,2-trimethylammonium-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl isophthalic acid-propenyl and 1-ethyl-2-methyl-2-propenyl.
Term " C
2-C
10-alkynyl " as used herein being meant have 2 to 10 carbon atoms and comprise the straight chain of at least one triple bond or the undersaturated hydrocarbyl group of branching; like ethynyl, third-1-alkynes-1-base, third-2-alkynes-1-base; n-fourth-1-alkynes-1-base; n-fourth-1-alkynes-3-base, n-fourth-1-alkynes-4-base, n-fourth-2-alkynes-1-base; n-penta-1-alkynes-1-base; n-penta-1-alkynes-3-base, n-penta-1-alkynes-4-base, n-penta-1-alkynes-5-base; N-penta-2-alkynes-1-base; N-penta-2-alkynes-4-base, n-penta-2-alkynes-5-base, 3-methyl fourth-1-alkynes-3-base, 3-methyl fourth-1-alkynes-4-base, n-oneself-1-alkynes-1-base, n-oneself-1-alkynes-3-base, n-oneself-1-alkynes-4-base, n-oneself-1-alkynes-5-base, n-oneself-1-alkynes-6-base, n-oneself-2-alkynes-1-base, n-oneself-2-alkynes-4-base, n-oneself-2-alkynes-5-base, n-oneself-2-alkynes-6-base, n-oneself-3-alkynes-1-base, n-oneself-3-alkynes-2-base, 3-methylpent-1-alkynes-1-base, 3-methylpent-1-alkynes-3-base, 3-methylpent-1-alkynes-4-base, 3-methylpent-1-alkynes-5-base, 4-methylpent-1-alkynes-1-base, 4-methylpent-2-alkynes-4-base or 4-methylpent-2-alkynes-5-base etc.
Term " C
2-C
10-fluorine haloalkenyl " or " C
2-C
10-fluorine alkynyl halide " as used herein being meant have 2 to 10 carbon atoms and comprise at least one two key, the straight chain of a triple bond or the undersaturated alkenyl or alkynyl group (as mentioned above) of branching respectively; and it carries at least one fluorine atom, and wherein some or all in the residual hydrogen atom can be with the separate halogen atom replacement that is selected from fluorine, bromine, chlorine or iodine in these groups.
Term " C
3-C
10-naphthenic base " as used herein being meant have 3 to 10 carbon atoms, particularly the monocyclic hydrocarbon residue of 3 to 8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl, ring octyl group, ring nonyl or ring decyl.
Term " C
3-C
10-fluorine halogen naphthenic base " the monocyclic hydrocarbon residue that is meant as used herein with 3 to 10 carbon atoms; it carries at least one fluorine atom, and wherein some or all in the residual hydrogen atom can be with the separate halogen atom replacement that is selected from fluorine, bromine, chlorine or iodine in these groups.
Term " partially or completely halogenated " means 1 in the Wasserstoffatoms or more a plurality of in the given residue, for example 1,2,3,4 or 5 or all with particularly fluorine or chlorine replacement of halogen atom.
About different method of use according to the present invention, particularly preferably be alone or in combination the following implication under each situation of substituting group and variable of 4-amino-thieno-[2,3-d]-pyrimidine compound of formula I:
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound preferably, wherein A is A2 and R
9Be selected from down group: hydrogen, C
1-C
10-alkyl or C
1-C
10-alkylhalide group.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound more preferably, wherein A is A2, R
8Be hydrogen R
9Be C
1-C
10-alkyl or C
1-C
10-alkylhalide group.
Particularly preferably be 4-amino-thieno-[2,3-d]-pyrimidine compound of those formulas I, wherein A is A2, R
8Be hydrogen R
9Be C
1-C
10-alkyl or C
1-C
10-alkylhalide group, and R wherein
8And R
9The substituting group at the chiral carbon atom place that is bonded to is (S)-configuration.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound most preferably, wherein A is A2, R
8Be hydrogen R
9Be methyl.
Particularly preferably be 4-amino-thieno-[2,3-d]-pyrimidine compound of those formulas I, wherein A is A2, R
8Be hydrogen R
9Be methyl, and R wherein
8And R
9The substituting group at the chiral carbon atom place that is bonded to is (S)-configuration.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R preferably
7Be hydrogen.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R preferably
6Be C
1-C
10-fluorine alkylhalide group.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R more preferably
6It is trifluoromethyl.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R preferably
3Be hydrogen.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R preferably
2Be selected from down group: hydrogen, halogen, C
1-C
10-alkyl and C
1-C
10-alkylhalide group.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R more preferably
2Be hydrogen.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R preferably
1Be selected from down group: hydrogen, halogen, C
1-C
10-alkyl and C
1-C
10-alkylhalide group.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound, wherein R more preferably
1Be hydrogen or chlorine.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound preferably, wherein X is a halogen.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound more preferably, wherein X is a chlorine.
4-amino-thieno-of formula I [2,3-d]-pyrimidine compound preferably, wherein n is 0.
Particularly preferably be 4-amino-thieno-[2, the 3-d]-said general formula I of pyrimidine-S compound:
N wherein, X, R
1, R
2, R
3, R
6, R
7And R
9Such as to formula I definition.
4-amino-thieno-of general formula I-S [2,3-d]-pyrimidine compound more preferably, X wherein, R
1, R
2, R
3, R
6, R
7And R
9Representative preceding text alone or in combination are to the preferred substituents of formula I definition.
4-amino-thieno-of general formula I-S [2,3-d]-pyrimidine compound most preferably, wherein n is 0 or 1, X is a chlorine, R
1Be hydrogen or halogen, R
2, R
3And R
7Be hydrogen, R
6Be C
1-C
10-fluorine alkylhalide group and R
9Be C
1-C
10-alkyl or C
1-C
10-alkylhalide group.
The preparation method
4-amino-thieno-[2 according to formula I of the present invention; 3-d] pyrimidine compound can prepare like the description among the WO 2007/135029 that relates to EP 0447 891B; Wherein 4-amino-thieno-[2,3-d] pyrimidine compound rises and starts from thiophene compound (II) and prepare.
In the presence of excessive phosphoryl halogen, for example 2 to 20mol phosphoryl chlorides or phosphoryl bromide are than 1mol (II), with formula (II) thiophene derivant
Wherein X and R
1Such as preceding text definition, react with dialkyl amide (III)
T wherein
1And T
2Be C independently of each other
1-C
4-alkyl or form 5 to 7-unit saturated heterocycles and R with nitrogen
2Such as preceding text definition, provide the thieno-of formula (Ia)-(2,3-d)-pyrimidine derivatives
R wherein
11It is chlorine or bromine.
Formula (Ia) compound that obtains as stated can replace 4 halogen atoms through other nucleophilic residues according to known method and transform, and said method is as being described in ' The Chemistry of Heterocyclic compounds ' " The pyrimidines "; D.J.Brown writes; J.Wiley & Sony, New York, London; Vol.16, (1962); Vol.16, Suppl.1, Vol.16, Suppl.2 (1985).
Use NR through describing like EP-A 447 891
3A replaces R
11, they are converted into corresponding formula I compound.
The instance of suitable dialkyl group-amides (III) is N, dinethylformamide, N, N-dimethyl--ethanamide, N, N-DEF, N, N-diethyl acetamide, N, N-dimethyl propylene acid amides and N, N-mesitylenic acid acid amides.
As mentioned above, reaction must be carried out comparing in the presence of excessive phosphoryl chloride or the phosphoryl bromide with thiophene derivant (II).Advantageously, reaction can be made solvent and takes place with phosphoryl halogen.Preferably, every mol thiophene derivant (II) uses 2 to 6mol phosphoryl halogens.
Usually, thiophene derivant (II) and N, the molar concentration rate of N-dialkyl amide (III) is 1: 1 to 1: 5.
Reaction is carried out in inert solvent usually, like chlorobenzene, and oil of mirbane, oil of Niobe, methylene dichloride; Dichlorobenzene, trichlorobenzene, ethyl benzoate, chloroform, tetracol phenixin; The N that preceding text are listed, one of N-dialkyl amide class, trichloroethane, hexamethyl phosphoric triamide (HMPT) or zellon.Preferred solvent is phosphoryl chloride and phosphoryl bromide or the listed N of preceding text, one of N-dialkyl amide class.
Be reflected at and have enough speed of response more than 20 ℃.In the temperature more than 150 ℃, atopic reduces.Preferably, the temperature that is reflected at 50 to 110 ℃ is carried out.
Through using the Lewis acid such as the Repone K of catalytic amount, sodium-chlor, iron(ic)chloride (III); Aluminum chloride, zinc chloride, tin chloride; Antimony pentafluoride, the catalyzer such as the N of boron trifluoride or titanium tetrachloride or use alkalescence, accelerine or N; The N-Diethyl Aniline can realize increasing yield and intensified response speed.
Other method of 4-amino-thieno-[2,3-d] pyrimidine compound of preparation formula I also is provided: according to general practice, with formula (IV) compound
Wherein X and R
1Such as preceding text definition, and contain residue R at least
2The acid anhydrides of-CO-or carboxylic acid R
2-COOH, or carboxylic acid and the reaction of lewis acidic adducts, wherein R
2Have aforesaid each implication, obtain formula (Ib) compound:
With phosphoryl halogen formula (Ib) compound is converted into as above formula (Ia) compound of definition.Suitable under specific situation is to carry out this conversion with two steps, through this separation of intermediates formula (VI) compound:
Usually, acid anhydrides or adducts with relativization compound (VI) 100 to 500mol-%, preferred 100 to 300mol-% amount is used.
Comprise at least one residue R
2The carboxylic acid anhydride of-CO-can be by dicarboxylicacid R
2-COOH such as PIVALIC ACID CRUDE (25), propionic acid or acetate provide; Perhaps by monocarboxylic acid R
2-COOH and an oxoacid such as phosphoric acid or sulfuric acid provide.
Preferred formic acid R
2-COOH has those of 1 to 4 carbon atom, particularly formic acid and acetate.
In addition, carboxylic acid R
2-COOH and Lewis acid such as zinc chloride, the adducts of boron trifluoride and titanium tetrachloride also suits.
Advantageously, from the conversion of (IV) to (Ib) in (10) to 150 ℃, preferred 20 to 120 ℃; More preferably 80 to 120 ℃ temperature, at inert solvent such as N, N-dialkyl amide class; N preferably, dinethylformamide and DMAC N,N; N-methyl-pyrrolidone, N carries out in N-dimethyl allene urea or the hexamethyl phosphoric triamide.
For separation of intermediates compound (VI), temperature of reaction should be selected from (10) to 80 ℃.
Usually, should be with relative carboxylic acid anhydride, excessive 1 to 10 times of carboxylic acid or carboxylic acid-Lewis acid-adducts, 1 to 5 times of preferred excessive ground add alkali such as triethylamine, N-methyl-pyrrolidone or N, accelerine.
Add water and remove reagent, like NSC 57182, or Vilsmeier reagent can accelerated reaction and increase formula (Ib) compound yield.
The oh group that formula (Ib) compound is 4 can replace with chlorine or bromine according to general practice, for example with phosphoryl chloride or phosphoryl bromide.
Finally, by the description of for example EP-A 447 891 4 chlorine and bromine are used NR
3A replaces.
NR
3A through the substituted aromatic yl group A of sulfo-can through each thiophenol with carry suitable leavings group for example the alkylation reaction of the fluoroalkylation compound of halogen atom prepare.
In addition, according to diagram 1, through using wherein R
12Be C
1-C
4The ortho ester of-alkyl (V) is converted into formula (VI) verivate with formula (II) thiophene compound, subsequently at amine NR
3There is cyclisation down in A, can obtain according to formula of the present invention (I) thieno-[2,3-d] pyrimidine compound.
Diagram 1:
The reaction scheme of up-to-date description is known in DE-A 26 54 090.Thiophene derivant (II) and (IV) can obtain according to the instruction that is disclosed in EP-A1 0,193 885.
In principle, the enantiomorph enrichment through substituted benzyl amine NR
3A can be through splitting corresponding racemic modification or obtaining via asymmetric synthesis from the achirality precursor.
Synthesis 2008,14, and 2283-2287 has described exemplary program, wherein lypase are used as racemic catalyzer through substituted benzyl amine chiral separation.According to following diagram 2, racemize is for example known from experience and little alkyl or alkenyl (R wherein
13Be C for example
1-C
4-alkyl, C
1-C
4-thiazolinyl and R
14Be for example optional substituted C
1-C
4-alkyl such as CH
2OCH
3) aliphatic carboxyl ester reaction, and after accomplishing reaction, a kind of enantiomorph can be converted into corresponding amide, and another kind of enantiomorph can keep unreacted.
Diagram 2:
R wherein
xLike preceding text to R
4, R
5, R
7Or R
8Define.
At R
xBe under the situation of little alkyl group such as methyl, typically, (S)-enantiomorph can be by acylations and (R)-enantiomorph can keep unreacted.Via distillation or after chromatography separates said reaction mixture, (R)-enantiomorph can directly use, and after according to following diagram 3 hydrolysis, after the cracking amido linkage, can obtain (S)-enantiomorph for example:
Diagram 3:
Obtaining the different synthesis program through the substituted benzyl amine enantiomorph enrichment or enantiomer-pure via asymmetric synthesis is described in the document.Typically, they involve the C=N key reduction of describing like diagram 4.The suitable substrate of the type reductive is oxime ethers (R for example
15=C
1-C
4-alkoxyl group), like for example Org.Lett.2007,9, the description of 1793-1795, perhaps chirality sulfimide (R for example
15=S (=O) tBu), like for example J.Org.Chem.2006,71, the description of 6859-6862.
Diagram 4:
In order to obtain to be suitable for the salt that agricultural or animal doctor use, can be in 0 to 150 ℃, preferred 20 to 120 ℃ TR 4-amino-thieno-[2,3-d] pyrimidine compound of formula I be reacted with conventional salt forming agent, such as hydrochloric acid; Hydrogen bromide, hydroiodic acid HI, sulfuric acid, phosphoric acid; Formic acid, acetate, oxalic acid, Phenylsulfonic acid; P-toluene-sulfonic acid, Witco 1298 Soft Acid, monobromethane, dimethyl sulphide acid esters or ethyl-sulfide acid esters.
Salify carries out in solvent or thinner usually.Suitable is aliphatic hydrocrbon n-pentane for example; N-hexane or sherwood oil; Aromatic hydrocarbon such as benzene, toluene or YLENE, benzyne or ethers such as diethyl ether, methyl-uncle's butyl ether, THF Huo diox, and ketone such as acetone, methyl ethyl ketone or MIPK; And halogenated hydrocarbon such as chlorobenzene, methylene dichloride, vinylchlorid, chloroform or zellon.Also can use the mixture of these solvents.
For the salt of preparation I compound, adopt reactant with stoichiometric ratio usually.Can use excessive one or another kind of component.
In the preparation method who describes, variable X, R
1, R
2And R
3Has the as above implication of definition, the implication of particularly preferably mentioning.
If each compound can not be via the preparation of above-mentioned approach, derivatize that then can be through other compound I or the conventional modification through described route of synthesis prepare them.
Said reaction mixture carries out aftertreatment in a usual manner, for example mixes, phase-splitting with water, and if suitable, through chromatography purification of crude product on alumina or silica gel for example.Some midbody and finished product can obtain with colourless or filbert thickness oily matter form, and it does not contain or removes volatile constituent at the following purifying of decompression and appropriate elevated temperature.If midbody and finished product obtain as solid, they can carry out purifying through recrystallization or lixiviate.
Insect
Formula I compound and salt thereof are particularly suitable for preventing and kill off effectively arthropod such as arachnids, thousand-legger (myriapedes) and insects and threadworms.
The animal pest of being prevented and kill off by formula I compound for example comprises:
Lepidopteran (Lepidoptera) insect, Agrotis ypsilon for example, yellow cutworm (Agrotis segetum), Alabama argillacea; Soybean noctuid (Anticarsia gemmatalis), apple silver moth (Argyresthia conjugella), Autographa gamma, loose powder butterfly geometrid moth (Bupalus piniarius); Cacoecia murinana, Capua reticulana, orchard autumn geometrid moth (Cheimatobia brumata), dragon spruce Choristoneura spp (Choristoneura fumiferana); Western dragon spruce Choristoneura spp (Choristoneura occidentalis), white point mythimna separata (Cirphis unipuncta), Pericarpium Mali pumilae steinernema (Cydia pomonella), Dendrolimus pini; Diaphania nitidalis, Diatraea grandiosella, Egyptian brill noctuid (Earias insulana), South America maize seedling phycitid (Elasmopalpus lignosellus); Ligustrum fine tortricidae (Eupoecilia ambiguella), Europe European pine shoot moth (Evetria bouliana), dirty noctuid (Feltia subterranea), the galleria mellonella waxmoth (Galleria mellonella) cut of grain skin; Lee's small kernel-eating insect (Grapholitha funebrana), oriental fruit months (Grapholitha molesta), bollworm (Heliothis armigera), Heliothis virescens (Heliothis virescens); Heliothis (Heliothis) Zea (Zea), Hellula undalis (Hellula undalis), Hibernia defoliaria, fall webworms (Hyphantria cunea); H griggles ermine moth (Yponomeuta malinellus), tomato stem gelechiid (Keiferia lycopersicella), Chinese hemlock spruce geometrid moth (Lambdina fiscellaria), Laphygma exigua; Leucoptera coffeella, pear leaf blister moth (Leucoptera scitella), Lithocolletis blancardella, Table Grape steinernema (Lobesia botrana); The wild snout moth's larva (Loxostege sticticalis) of net awl volume, gypsymoth (Lymantria dispar), lymantria monacha (Lymantria monacha), peach leaf miner (Lyonetia clerkella); Malacosoma neustria (Malacosoma neustria), lopper worm (Mamestra brassicae), Douglas fir are closed poison moth (Orgyia pseudotsugata), European corn borer (Ostrinia nubilalis); Small noctuid (Panolis flammea), pink bollworm (Pectinophora gossypiella), boundary noctuid (Peridroma saucia), circle palm boat moth (Phalera bucephala); Potato tuberworm (Phthorimaea operculella), oranges and tangerines leaf lyonetid (Phyllocnistis citrella), Pieris brassicae (Pieris brassicae), the green noctuid of clover (Plathypena scabra); Small cabbage moth (Plutella xylostella), soybean chi noctuid (Pseudoplusia includens), U.S. European pine shoot moth (Rhyacionia frustrana); Scrobipalpula absoluta, gelechiid (Sitotroga cerealella), pilleriana (Sparganothis pilleriana); Fall army worm (Spodoptera frugiperda), Spodoptera littoralis (Spodoptera littoralis), twill are coveted noctuid (Spodoptera litura); Thaumatopoea pityocampa, the green volume of oak moth (Tortrix viridana), amyloid plaque noctuid (Trichoplusia ni) and dragon spruce line steinernema (Zeiraphera canadensis);
Beetle (Coleoptera (Coleoptera)), the narrow lucky fourth of pears (Agrilus sinuatus) for example, vertical bar click beetle (Agriotes lineatus), dark click beetle (Agriotes obscurus); Amphimallus solstitialis, North Sea timber bark beetle (Anisandrus dispar), cotton boll resembles (Anthonomus grandis), and the umbrella flower resembles (Anthonomus pomorum); Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis (Atomaria linearis), vertical pit cutting pin small moth (Blastophagus piniperda); Blitophaga undata, broad bean weevil (Bruchus rufimanus), pea weevil (Bruchus pisorum), Bruchus lentis; The green volume of birch resembles (Byctiscus betulae), the big tortoise plastron of beet (Cassida nebulosa), Kidney bean firefly chrysomelid (Cerotoma trifurcata), golden flower cockchafer (Cetonia aurata); Chinese cabbage seed tortoise resembles (Ceuthorrhynchus assimilis), Ceuthorrhynchus napi, the recessed shin flea beetle of flea (Chaetocnema tibialis); Tobacco click beetle (Conoderus vespertinus), officinalis scotellaris (Crioceris asparagi), Ctenicera ssp.; Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata; Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis; Tobacco flea beetle (Epitrix hirtipennis), the chain cotton ash covers and resembles (Eutinobothrus brasiliensis), European hylobius abietis (Hylobius abietis); Egyptian Herba Medicaginis leaf resembles (Hypera brunneipennis), and alfalfa leaf resembles (Hypera postica), ips typographus (Ips typographus); Tobacco scotellaris (Lema bilineata), Lema melanopus, colorado potato beetles (Leptinotarsa decemlineata); Beet click beetle (Limonius californicus), rice water resembles (Lissorhoptrus oryzophilus), Melanotus communis; Meligethes aeneus, Da Li gill cockchafer (Melolontha hippocastani), gill cockchafer in May (Melolontha melolontha); Oulema oryzae (Oulema oryzae), black grape ear image (Otiorrhynchus sulcatus), strawberry root ear resembles (Otiorrhynchus ovatus); Horseradish ape chrysomelid (Phaedon cochleariae), leaf of pear tree resembles (Phyllobius pyri), Phyllotreta chrysocephala; Food phyllobranchia cockchafer belongs to (Phyllophaga sp.), and rutelian (Phyllopertha horticola) is sent out in the flower garden, green chest dish flea beetle (Phyllotreta nemorum); Phyllotreta striolata (Phyllotreta striolata), Japan popillia flavosellata fairmaire (Popillia japonica), vertical bar root nodule resemble (Sitona lineatus) and grain weevil (Sitophilus granaria);
Fly, mosquito class (Diptera (Diptera)), Aedes aegypti (Aedes aegypti) for example, informal voucher yellow-fever mosquito (Aedes albopictus), Aedes vexans (Aedes vexans), Mexico is by trypetid (Anastrepha ludens); Anopheles maculipennis (Anopheles maculipennis), Anopheles crucians, Anopheles albimanus, anopheles costalis (Anopheles gambiae), Anopheles freeborni; Anopheles leucosphyrus, anopheles minius (Anopheles minimus), anopheles quadrimaculatus (Anopheles quadrimaculatus), calliphora erythrocephala (Calliphora vicina), Mediterranean fruitfly (Ceratitis capitata); Maggot disease gold fly (Chrysomya bezziana), Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea; Chrysops atlanticus, cochliomyia bominovorax (Cochliomyia hominivorax), Chinese sorghum health cecidomyiia (Contarinia sorghicola), cordylobia anthropophaga (Cordylobia anthropophaga), Culicoides furens; Northern house (Culex pipiens), Culex nigripalpus, Culex quinquefasciatus (Culex quinquefasciatus), Culex tarsalis, Culiseta inornata; Culiseta melanura, the few hair on the neck trypetid (Dacus cucurbitae) of melon, Fructus oleae europaeae fruit fly (Dacus oleae), rape leave cecidomyiia (Dasineura brassicae), fly (Delia antique) is planted on green onion ground; Wheat field kind fly (Delia coarctata), delia platura (Delia platura), fly (Delia radicum), human botfly (Dermatobia hominis), Fannia canicularis (Fannia canicularis) are planted in wild cabbage ground; 3 chi standing grain flies (Geomyza tripunctata), Gasterophilus intestinalis (Gasterophilus intestinalis), glossina morsitans (Glossina morsitans), glossina palpalis (Glossina palpalis), brown sufficient tsetse fly (Glossina fuscipes); Plan is posted tsetse fly (Glossina tachinoides), west horn fly (Haematobia irritans), saddle cecidomyiia (Haplodiplosis equestris), Hippelates spp., delia platura (Hylemyia platura); Hypoderma lineata, Leptoconops torrens, vegetables liriomyza bryoniae (Liriomyza sativae), trifolium liriomyza bryoniae (Liriomyza trifolii), Lucilia caprina; Lucilia cuprina (Lucilia cuprina), lucilia sericata (Lucilia sericata), Lycoria pectoralis, Mansonia titillanus, hessian fly (Mayetiola destructor); Face fly (Musca autumnalis), housefly (Musca domestica), false stable fly (Muscina stabulans), Oestrus ovis (Oestrus ovis), standing grain fly (Opomyza florum); Oscinella frit (Oscinella frit), spinach spring fly (Pegomya hysocyami), Phorbia antiqua, fly (Phorbia brassicae), Phorbia coarctata are planted in radish ground; Phlebotomus argentipes, Psorophora columbiae, carrot fly (Psila rosae), Psorophora discolor, Prosimulium mixtum; Cherry is around trypetid (Rhagoletis cerasi), and apple is around trypetid (Rhagoletis pomonella), Sarcophaga haemorrhoidalis, Sarcophaga (Sarcophaga spp.); Simulium vittatum, tatukira (Stomoxys calcitrans) is had a liking for the gadfly (Tabanus bovinus), Tabanus atratus; Tabanus lineola, Tabanus similis, Tipula oleracea and European daddy-longlegs (Tipula paludosa);
Thrips class (Thysanoptera (Thysanoptera)), Dichromothrips corbetti for example, dichromatism Thrips (Dichromothrips) ssp.; Frankliniella fusca, Frankliniella occidentalis (Frankliniella occidentalis), east flower thrips (Frankliniella tritici); Scirtothrips citri; Rice thrips (Thrips oryzae), palm thrips (Thrips palmi) and onion thrips (Thrips tabaci)
White ants (Isoptera (Isoptera)), Calotermes flavicollis for example, Leucotermes flavipes; Heterotermes aureus; American-European reticulitermes flavipe (Reticulitermes flavipes), Reticulitermes virginicus (Reticulitermes virginicus), black dull reticulitermes flavipe (Reticulitermes lucifugus); Sang Te reticulitermes flavipe (Reticulitermes santonensis); Reticulitermes grassei, Termes natalensis and Taiwan formosanes (Coptotermes formosanus);
Blattidae (Blattodea (Blattaria)-Blattodea (Blattodea)), Groton bug (Blattella germanica) for example, Blattella asahinae; Periplaneta americana (Periplaneta americana); Periplaneta japan, the big Lian of foxiness (Periplaneta brunnea), Peroplaneta fluligginosa (Periplaneta fuligginosa); Australian cockroach (Periplaneta australasiae), and oriental cockroach (Blatta orientalis);
Bedbug class, Phytophthira, leafhopper class, aleyrodid class, a red-spotted lizard class, cicada class (Hemiptera (Hemiptera)) are for example intended green stinkbug (Acrosternum hilare), America paddy bar chinch bug (Blissus leucopterus), blackspot cigarette fleahopper (Cyrtopeltis notatus), red cotton bug (Dysdercus cingulatus); Dysdercus intermedius, wheat Eurygasterspp (Eurygaster integriceps), brown America stinkbug (Euschistus impictivntris), cotton boll beak coried (Leptoglossus phyllopus), U.S. tarnished plant bug (Lygus lineolaris); Tarnished plant bug (Lygus pratensis), Nezara viridula smaragdula Fabricius. (Nezara viridula), square butt stinkbug (Piesma quadrata), Solubea insularis, Thyanta perditor; Acyrthosiphon onobrychis, adelge laricis (Adelges laricis), Aphidula nasturtii, beans winged euonymus aphid (Aphis fabae), strawberry root aphid (Aphis forbesi); Apple aphid (Aphis pomi), cotten aphid (Aphis gossypii), North America bitter edible plant Fischer aphid (Aphis grossulariae), Xi Naide aphid (Aphis schneideri), different spiraea aphid (Aphis spiraecola); Williams Elder Twig aphid (Aphis sambuci), acyrthosiphum pisim (Acyrthosiphon pisum), the potato ditch does not have net aphid (Aulacorthum solani), Bemisia argentifolii (Bemisia argentifolii), welted thistle short-tail aphid (Brachycaudus cardui); Lee's short-tail aphid (Brachycaudus helichrysi), peach short-tail aphid (Brachycaudus persicae), cherry short-tail aphid (Brachycaudus prunicola), brevicoryne brassicae (Brevicoryne brassicae), Capitophorus horni; Cerosipha gossypii, knurl nail hair aphid (Chaetosiphon fragaefolii) in the strawberry, the tea Fischer conceals knurl aphid (Cryptomyzus ribis), abies nordmanniana vertebra adelgid (Dreyfusia nordmannianae), dragon spruce conisphere aphid (Dreyfusia piceae); Ju Genxi rounded tail aphid (Dysaphis radicola), Dysaulacorthum pseudosolani, western rounded tail aphid (Dysaphis plantaginea) before the car, Dysaphis pyri, silkworm worm smaller green leaf hopper (Empoasca fabae); Mealy plum aphid (Hyalopterus pruni), the bitter ultra knurl aphid of dish (Hyperomyzus lactucae) of tea Fischer, grain aphid (Macrosiphum avenae), potato aphid (Macrosiphum euphorbiae); Macrosiphon rosae, Megoura viciae (Megoura viciae), Melanaphis pyrarius, wheat does not have net aphid (metopolophium dirhodum); Black peach aphid (Myzus persicae), shallot knurl aphid (Myzus ascalonicus), cherry knurl aphid (Myzus cerasi), Rhizoma Dioscoreae Bulbiferae knurl aphid (Myzus varians); Lettuce is patched up Macrosiphus spp (Nasonovia ribis-nigri), brown paddy plant hopper (Nilaparvata lugens), handle goitre woolly aphid (Pemphigus bursarius), the flat angle of sugarcane plant hopper (Perkinsiella saccharicida); Phorodon aphid (Phorodon humuli), apple sucker (Psylla mali), Psylla piri, the shallot knurl aphid (Rhopalomyzus ascalonicus) of hanging; Corn Rhopalosiphum spp (Rhopalosiphum maidis), rhopalosiphum padi (Rhopalosiphum padi), apple Rhopalosiphum spp (Rhopalosiphum insertum), Sappaphis mala; Sappaphis mali, green bugs (Schizaphis graminum), elm pears woolly aphid (Schizoneura lanuginosa), grain aphid (Sitobion avenae); Greenhouse whitefly (Trialeurodes vaporariorum), tangerine sound aphid (Toxoptera aurantii) and, grape phylloxera (Viteus vitifolii), bed bug (Cimex lectularius); Cimex hemipterus (Cimex hemipterus), Reduvius senilis, the vertebra Reduvius (Triatoma spp.) and the back of tooth are hunted stinkbug (Arilus critatus);
Ant, honeybee, wasp, sawfly (Hymenoptera (Hymenoptera)), cabbage sawfly (Athalia rosae) for example, Atta cephalotes, Atta capiguara; Atta cephalotes, Atta laevigata, Atta robusta, leaf cutting ant (Atta sexdens); Dezhou leaf cutting ant (Atta texana) is lifted abdomen uranotaenia (Crematogaster) spp., prune sawfly (Hoplocampa minuta), apple fertile leaf honeybee (Hoplocampa testudinea); Black wool ant (Lasius niger), MonomoriumMayr (Monomorium pharaonis), fiery ant (Solenopsis geminata), Argentinian fiery ant (Solenopsis invicta); Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus; Brown major part ant (Pheidole megacephala), Dasymutilla occidentalis, bombus (Bombus) spp.; Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica; Paravespula germanica, Dolichovespula maculata, Vespa crabro; Polistes rubiginosa, Camponotus floridanus and Linepithema humile;
Cricket, grasshopper, locust (Orthoptera (Orthoptera)), for example tame Xi (Acheta domestica), European mole cricket (Gryllotalpa gryllotalpa); Asia migratory locusts (Locusta migratoria), biobelt are deceived locust (Melanoplus bivittatus), and red shin is deceived locust (Melanoplus femurrubrum); Mexico deceives locust (Melanoplus mexicanus), and blood is deceived locust (Melanoplus sanguinipes), the withered black locust of stone (Melanoplus spretus); Red locust (Nomadacris septemfasciata), America desert locust (Schistocerca americana), desert locust (Schistocerca gregaria); Morocco halberd line locust (Dociostaurus maroccanus), greenhouse weta (Tachycines asynamorus), plug is received jar (unit of capacitance) dolly locust (Oedaleus senegalensis); Zonozerus variegatus; Africa sugarcane locust (Hieroglyphus daganensis), sissoo locust (Kraussaria angulifera), Italian locust (Calliptamus italicus); Dwell locust (Chortoicetes terminifera) and brownly fly to intend migratory locusts (Locustana pardalina) of Australia grass;
Arachnida is like arachnids (acarina (Acarina)), for example soft ticks section (Argasidae); Hard tick section (Ixodidae) and Sarcoptidae (Sarcoptidae), like lone star tick (Amblyomma americanum), illuminated flower tick (Amblyomma variegatum); Spot flower tick (Ambryomma maculatum) is arranged, adobe tick (Argas persicus), Boophilus annulatus (Boophilus annulatus); Boophilus decoloratus (Boophilus decoloratus), boophilus microplus (Boophilus microplus), dermacentor silvarum (Dermacentor silvarum); Dermacentor andersoni (Dermacentor andersoni), Dermacentor variabilis (Dermacentor variabilis), Hyalomma truncatum; Castor bean tick (Ixodes ricinus), Ixodes rubicundus, Ixodes scapularis; Ixodes holocyclus (Ixodes holocyclus), Ixodes pacificus, tampan tick belongs to (Ornithodorus moubata); Ornithodorus hermsi, Ornithodorus turicata, ornithonyssus bacoti (Ornithonyssus bacoti); Otobius megnini, Dermanyssus gallinae (Dermanyssus gallinae), sheep scabies mite (Psoroptes ovis); Brown dog tick (Rhipicephalus sanguineus), rhipicephalus appendiculatus (Rhipicephalus appendiculatus), Rhipicephalus evertsi; Sarcoptes scabiei hominis (Sarcoptes scabiei), and Eriophyidae (Eriophyidae spp.) Ru Sishi acupuncture goitre mite (Aculus schlechtendali), oranges and tangerines wrinkle leaf Aculus (Phyllocoptrata oleivora) and Eriophyes sheldoni; Tarsonemidae (Tarsonemidae spp.) is like primrose herbivore mite (Phytonemus pallidus) and Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus); Tenuipalpidae (Tenuipalpidae spp.) is like purplish red short hairs mite (Brevipalpus phoenicis); Tetranychidae (Tetranychidae spp.) is like carmine spider mite (Tetranychus cinnabarinus); Refreshing Ze Shi tetranychid (Tetranychus kanzawai); Pacific Ocean tetranychid (Tetranychus pacificus), 2 tetranychids of linden (Tetranychus telarius) and Tetranychus urticae (Tetranychus urticae), panonychus ulmi (Panonychus ulmi); Panonychus citri (Panonychus citri) and meadow unguiculus mite (Oligonychus pratensis); Spider shape order (Araneida), for example erythema spider (Latrodectus mactans) and brown flat first spider (Loxosceles reclusa);
Flea class (Siphonaptera (Siphonaptera)); Ctenocephalides felis (Ctenocephalides felis) for example, ctenocephalides canis (Ctenocephalides canis), Xanthopsyllacheopis (Xenopsylla cheopis); Pulex irritans (Pulex irritans); Chigo (Tunga penetrans), and ceratophyllus fasciatus (Nosopsyllus fasciatus)
Silverfish, tame silverfish (Thysanura (Thysanura)), for example Taiwan silverfish (Lepisma saccharina) and tame silverfish (Thermobia domestica),
Centipede (chilopoda (Chilopoda)), Scutigera coleoptrata,
Thousand-legger (Diplopoda (Diplopoda)), Narceus spp. for example,
Earwig (Dermaptera (Dermaptera)), Forficula auricularia for example,
Lice class (Anoplura (Phthiraptera)), head louse (Pediculus humanus capitis) for example, Pediculus (Pediculus humanus corporis; Pthirus pubis, haematopinus eurysternus (Haematopinus eurysternus), haematopinus suis (Haematopinus suis); Linognathus vituli (Linognathus vituli); Bovicola bovis, Menopon gallinae, chick poultry louse (Menacanthus stramineus) and ox pipe lice (Solenopotes capillatus).
Collembola (Collembola) (springtail), for example Onychiurus ssp..
They also are suitable for preventing and kill off threadworms: plant nematode class such as root knot nematode; North root knot nematode (Meloidogyne hapla); Meloidogyne incognita (Meloidogyne incognita); Javanese root knot nematode (Meloidogyne javanica) and other Meloidogyne (Meloidogyne); Sporangiocyst-formation threadworms; Globodera rostochiensis (Globodera rostochiensis) and other ball Heterodera (Globodera); Heterodera avenae, soybean cyst nematode (Heterodera glycines), beet golden nematode (Heterodera schachtii); Trifolium golden nematode (Heterodera trifolii) and other Heterodera (Heterodera); Plant the goitre threadworms, goitre Turbatrix (Anguina); Stem and blade face threadworms, Aphelenchoides (Aphelenchoides); The thorn threadworms, long-tail thorn nematode (Belonolaimus longicaudatus) and other thorn Turbatrix (Belonolaimus); The loose ends insects, pine wood nematode (Bursaphelenchus xylophilus) and other umbrella Aphelenchoides (Bursaphelenchus); The loop wire insects, Criconema, Criconemella, Criconemoides, a loop wire Eimeria (Mesocriconema); Stem and bulb threadworms, potato haulm nematode (Ditylenchus destructor), fuller's teasel Ditylenchus dipsaci (Ditylenchus dipsaci) and other Ditylenchus (Ditylenchus); The awl threadworms, awl Turbatrix (Dolichodorus); The spiral-line insects, Heliocotylenchus multicinctus and other spiral-line Eimeria (Helicotylenchus); Sheath with intend the sheath threadworms, sheath Turbatrix (Hemicycliophora) and partly take turns Turbatrix (Hemicriconemoides); Hirshmanniella; The tie threadworms, tie Turbatrix (Hoploaimus); Pseudo-root knot nematode class, natural pearls Turbatrix (Nacobbus); The minute hand threadworms, ease is removed minute hand nematode (Longidorus elongatus) and other minute hand Turbatrix (Longidorus); Root spot nematode; Unelected Pratylenchidae (Pratylenchus neglectus); Cobb root (Pratylenchus penetrans), Pratylenchus curvitatus, Gooch Pratylenchidae (Pratylenchus goodeyi) and other Pratylenchidae belong to (Pratylenchus); The threadworms that hides, similar similes thorne (Radopholus similis) and other perforation line Eimeria (Radopholus); Kidney shape threadworms, the strong nematode that spirals (Rotylenchus robustus) and other Turbatrix that spirals (Rotylenchus); Peltate Turbatrix (Scutellonema); Tubbiness root threadworms, original burr nematode (Trichodorus primitivus) and other burr Turbatrix (Trichodorus), type burr Turbatrix (Paratrichodorus); Downgrade threadworms, the Clayton downgrades nematode (Tylenchorhynchus claytoni), and indefinite dwarfing nematode (Tylenchorhynchus dubius) and other are downgraded Turbatrix (Tylenchorhynchus); The Citrus threadworms, pulvinulus sword Turbatrix (Tylenchulus); The sword nematode class, Xiphinema (Xiphinema); With other plant parasitic nematodes kind.
Formula I compound and salt thereof also are used to prevent and kill off arachnids (Arachnoidea), like acarine (acarina (Acarina)), for example soft ticks section (Argasidae); Hard tick section (Ixodidae) and Sarcoptidae (Sarcoptidae), lone star tick (Amblyomma americanum), illuminated flower tick (Amblyomma variegatum); Adobe tick (Argas persicus), Boophilus annulatus (Boophilus annulatus), boophilus decoloratus (Boophilus decoloratus); Boophilus microplus (Boophilus microplus), dermacentor silvarum (Dermacentor silvarum), Hyalomma truncatum; Castor bean tick (Ixodes ricinus), Ixodes rubicundus, tampan tick belongs to (Ornithodorus moubata); Otobius megnini; Dermanyssus gallinae (Dermanyssus gallinae), sheep scabies mite (Psoroptes ovis), rhipicephalus appendiculatus (Rhipicephalus appendiculatus); Rhipicephalus evertsi; Sarcoptes scabiei hominis (Sarcoptes scabiei), and Eriophyidae (Eriophyidae spp.) Ru Sishi acupuncture goitre mite (Aculus schlechtendali), oranges and tangerines wrinkle leaf Aculus (Phyllocoptrata oleivora) and Eriophyes sheldoni; Tarsonemidae (Tarsonemidae spp.) is like primrose herbivore mite (Phytonemus pallidus) and Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus); Tenuipalpidae (Tenuipalpidae spp.) is like purplish red short hairs mite (Brevipalpus phoenicis); Tetranychidae (Tetranychidae spp.) is like carmine spider mite (Tetranychus cinnabarinus); Refreshing Ze Shi tetranychid (Tetranychus kanzawai); Pacific Ocean tetranychid (Tetranychus pacificus), 2 tetranychids of linden (Tetranychus telarius) and Tetranychus urticae (Tetranychus urticae), panonychus ulmi (Panonychus ulmi); Panonychus citri (Panonychus citri) and meadow unguiculus mite (Oligonychus pratensis).
Formula I compound is prevented and kill off insect particularly usefully, preferably suckes juice or boring insects such as following insects: Thysanoptera (Thysanoptera), Diptera (Diptera) and Hemiptera (Hemiptera); Particularly following kind:
Thysanoptera (Thysanoptera): Frankliniella fusca; Frankliniella occidentalis (Frankliniella occidentalis); East flower thrips (Frankliniella tritici); Scirtothrips citri, rice thrips (Thrips oryzae), palm thrips (Thrips palmi) and onion thrips (Thrips tabaci);
Diptera, Aedes aegypti for example, the informal voucher yellow-fever mosquito, Aedes vexans, Mexico is by trypetid, anopheles maculipennis, Anopheles crucians; Anopheles albimanus, anopheles costalis, Anopheles freeborni, Anopheles leucosphyrus, anopheles minius, anopheles quadrimaculatus, calliphora erythrocephala; Mediterranean fruitfly, maggot disease gold fly, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus; Cochliomyia bominovorax, Chinese sorghum health cecidomyiia, cordylobia anthropophaga, Culicoides furens, northern house, Culex nigripalpus, Culex quinquefasciatus; Culex tarsalis, Culiseta inornata, Culiseta melanura, the few hair on the neck trypetid of melon, the Fructus oleae europaeae fruit fly, the rape leave cecidomyiia, fly is planted on green onion ground; Wheat field kind fly, delia platura, fly, human botfly, Fannia canicularis, 3 chi standing grain flies, Gasterophilus intestinalis are planted in wild cabbage ground; Glossina morsitans, glossina palpalis, brown sufficient tsetse fly is intended and posts tsetse fly, west horn fly, saddle cecidomyiia, Hippelates spp.; Delia platura, Hypoderma lineata, Leptoconops torrens, vegetables liriomyza bryoniae, trifolium liriomyza bryoniae, Lucilia caprina, lucilia cuprina; Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, hessian fly, face fly, housefly, false stable fly; Oestrus ovis, the standing grain fly, Oscinella frit, spinach spring fly, Phorbia antiqua, fly is planted on radish ground; Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, carrot fly, Psorophora discolor, Prosimulium mixtum; Cherry is around trypetid, and apple is around trypetid, Sarcophaga haemorrhoidalis, Sarcophaga, Simulium vittatum, tatukira; Have a liking for the gadfly, Tabanus atratus, Tabanus lineola, Tabanus similis, Tipula oleracea and European daddy-longlegs;
Hemiptera (Hemiptera), Acyrthosiphon onobrychis, adelge laricis, Aphidula nasturtii, beans winged euonymus aphid, strawberry root aphid, apple aphid; Cotten aphid, North America bitter edible plant Fischer aphid, the Xi Naide aphid, different spiraea aphid, the Williams Elder Twig aphid, acyrthosiphum pisim, the potato ditch does not have the net aphid; Welted thistle short-tail aphid, Lee's short-tail aphid, peach short-tail aphid, cherry short-tail aphid, brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii; Knurl nail hair aphid in the strawberry, the tea Fischer conceals the knurl aphid, abies nordmanniana vertebra adelgid, dragon spruce conisphere aphid, Ju Genxi rounded tail aphid, Dysaulacorthum pseudosolani, western rounded tail aphid before the car; Dysaphis pyri, silkworm worm smaller green leaf hopper, mealy plum aphid, the ultra knurl aphid of the bitter dish of tea Fischer, grain aphid, potato aphid, Macrosiphon rosae; Megoura viciae, Melanaphis pyrarius, wheat does not have the net aphid, Myzodes persicae, shallot knurl aphid, cherry knurl aphid, Rhizoma Dioscoreae Bulbiferae knurl aphid; Lettuce is patched up Macrosiphus spp, brown paddy plant hopper, handle goitre woolly aphid, the flat angle of sugarcane plant hopper, phorodon aphid, apple sucker, Psylla piri; The shallot knurl aphid of hanging, corn Rhopalosiphum spp, rhopalosiphum padi, apple Rhopalosiphum spp, Sappaphis mala, Sappaphis mali; Green bugs, elm pears woolly aphid, grain aphid, greenhouse whitefly, tangerine sound aphid, and grape phylloxera;
Formula I compound is prevented and kill off the insects of Hemiptera (Hemiptera) and Thysanoptera (Thysanoptera) particularly usefully.
Preparaton
In order to be used for according to the method for the invention, can formula I compound be converted into conventional preparaton, for example solution, emulsion, suspension-s, dirt agent, pulvis, paste, granule and the solution that directly can spray.Type of service depends on specific purposes and application process.Select preparaton and application process to guarantee under each situation meticulous and uniform distribution according to formula I compound of the present invention.
Preparaton prepares (referring to for example summarizing US 3,060,084, EP-A 707 445 (liquid concentrate), Browning, " Agglomeration ", Chemical Engineering in a known way; Dec.4,1967,147-48, Perry ' s Chemical Engineer ' s Handbook, 4th Ed., McGraw-Hill, New York; 1963, the 8-57 pages or leaves with and following WO 91/13546, US 4,172,714, US 4,144; 050, US 3,920,442, and US 5,180, and 587; US 5,232,701, and US 5,208,030, and GB 2; 095,558, US 3,299,566, Klingman, Weed Control as a Science; John Wiley and Sons, Inc., New York, 1961, people such as Hance, Weed Control Handbook; 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann; A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001,2.D.A.Knowles; Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example through expanding active compound with the auxiliary agent that is suitable for the formulating agrochemical article, said auxiliary agent is like solvent and/or carrier; If the emulsifying agent of hoping, tensio-active agent and dispersion agent, preserving agent, skimmer, antifreezing agent, also optional for the seed treatment agent preparaton is tinting material and/or tackiness agent and/or gelatinizing agent.
The suitable solvent/carrier for example is:
-solvent, like water, aromatic solvent (for example Solvesso product, YLENE etc.); Alkane (for example mineral level branch), alcohols (methyl alcohol for example, butanols, amylalcohol; Phenylcarbinol), ketone (for example pimelinketone, gamma-butyrolactone), pyrrolidone (N-methyl-pyrrolidone (NMP), N-octylpyrrolidone NOP), acetic ester (oxalic acid diol ester); Alkyl lactate ester, lactone such as g-GBL, glycols, lipid acid diformamide; Lipid acid and fatty acid ester, triglyceride level, the oil of plant or animal-origin and oil such as alkanisation vegetables oil through modifying.Also can use solvent mixture in principle.
-carrier, like ground natural mineral and ground synthetic mineral, like silica gel, finely divided silicic acid, silicates, talcum powder; Kaolin, Attaclay, Wingdale, lime, chalk, terra miraculosa; Loess, clay, rhombspar, zeyssatite, calcium sulfate and sal epsom, Natural manganese dioxide; The ground synthetic materials, fertilizer, ammonium sulfate for example, ammonium phosphate, an ammonium nitrate, the product of ureas and plant origin such as flour, tree bark powder, wood powder and nutshell powder, cellulose powder and other solid carrier.
Examples of suitable emulsifiers is non-ionic type and anionic emulsifier (for example polyoxy ethene Fatty Alcohol(C12-C14 and C12-C18) ethers, AS and arylsulphonate).
The instance of dispersion agent is xylogen-sulfite waste lye and methylcellulose gum.
Suitable tensio-active agent comprises following basic metal; Earth alkali metal and ammonium salt: lignin sulfonic acid, naphthene sulfonic acid, sulfocarbolic acid, dibutyl naphthene sulfonic acid, alkyl aryl sulfonate, alkyl sulfuric ester, alkyl sulfonic ester; Fatty alcohol sulfate, lipid acid and Sulfated Fatty Alcohol(C12-C14 and C12-C18) glycol ethers; The condenses that further comprises sulfonated naphthalene and naphthalene derivatives and formaldehyde, the condenses of naphthalene or naphthene sulfonic acid and phenol and formaldehyde, polyoxy ethene octyl phenyl ether, ethoxylation isooctyl phenol; Octyl phenol, nonylphenol, alkyl phenyl polyglycol ether; Tributyl phenyl polyglycol ether, three stearyl phenyl polyglycol ethers, alkyl aryl polyether alcohol class; Pure and mild Fatty Alcohol(C12-C14 and C12-C18)/ethylene oxide condensate, ethoxylated castor oil, Voranol EP 2001; Ethoxylation polyoxy propylene, lauryl alcohol polyglycol ether acetal and sorbitol ester class.
Can also be with antithrombotics such as glycerine, 1, Ucar 35 and sterilant add preparaton.
Suitable skimmer be for example skimmer based on silicon or Magnesium Stearate.
Suitable preserving agent for example comprises dichlorophen (dichlorophen) and phenylcarbinol hemiformal.
Suitable thickening material comprises compound, and it can give preparaton, HV and agitation phase LV when promptly static with the pseudo-plasticity behavior of flowing.For example in this context, can mention commercial thickening material based on polyose; Like XG 550
(Kelzan
; From Kelco); Rhodopol
23 (Rhone Poulenc) or Veegum
(from R.T.Vanderbilt); Perhaps organic phyllosilicate is like Attaclay
(from Engelhardt).Be suitable for according to the skimmer of dispersion liquid of the present invention be; For example; Silicone emulsion (Silikon
SRE for example; Wacker or Rhodorsil
; From Rhodia); The long-chain alcohols, lipid acid, organofluorine compound and composition thereof.Can add biocide comes stabilization compsn according to the present invention to attack with combating microorganisms.Suitable biocides such as those based isothiazolones such as Avecia trademark of Proxel
(or Arch) or Thor? Chemie's Acticide
RS and Rohm? &? Haas's Kathon
MK sales compounds.Suitable frostproofer is an organic polyhydric alcohol, for example 1, Ucar 35 or glycerine.These adopt with the amount that is no more than 10 weight % usually, based on the active compound combinations gross weight.If it is suitable; The buffer reagent that can comprise by total amount 1 to the 5 weight % of prepared preparaton according to active compound combinations of the present invention is used for regulating pH, and the amount of used buffer reagent and type depend on the chemical property of active compound or various active compound.The instance of buffer reagent a little less than being inorganic or organic acid for example phosphoric acid, alkyl for an alkali metal salt of boric acid, acetate, propionic acid, Hydrocerol A, fumaric acid, tartrate, oxalic acid and succsinic acid.
During comprising, the material that is suitable for preparing solution, emulsion, paste or the oily dispersion liquid that directly can spray,, further comprises the oil of coal tar and plant or animal-origin like kerosene or diesel oil to the MO level branch of high boiling point; Aliphatic series, ring-type and aromatic hydrocarbon be the naphthalene of toluene, YLENE, paraffin, tetralin, alkanisation or their verivate for example, methyl alcohol, ethanol; Propyl alcohol, butanols, hexalin; Pimelinketone, isophorone, intensive polar solvent be methyl-sulphoxide, N-Methyl pyrrolidone and water for example.
Pulvis, diffusion material and dirt agent can prepare through active substance and solid carrier are mixed together or grind.
Granule for example coatedgranules, impregnated granules agent and homogeneous particle agent can prepare through activeconstituents is bonded to solid carrier.The instance of solid carrier is that mineral are native like silica gel, silicates, talcum powder, kaolin, Attaclay; Wingdale, lime, chalk, terra miraculosa, loess; Clay, rhombspar, zeyssatite, calcium sulfate, sal epsom; Natural manganese dioxide, ground synthetic materials, fertilizer is product such as flour, tree bark powder, wood powder and nutshell powder, cellulose powder and other solid carrier of ammonium sulfate, ammonium phosphate, an ammonium nitrate, ureas and plant origin for example.
Generally speaking, preparaton comprises 0.01 to 95 weight %, the activeconstituents of preferred 0.1 to 90 weight %.Activeconstituents is with 90% to 100%, and preferred 95% to 100% (according to the NMR spectrum) purity adopts.
For the seed treatment purpose, can be doubly with each preparaton dilution 2-10, what obtain promptly counts 0.01 to 60 weight % with the concentration of preparation by active compound weight, preferred 0.1 to 40 weight %.
Formula I compound can former state, with their preparaton form or from the type of service of its preparation; For example with solution, powder, suspension-s or dispersion liquid, emulsion, oily dispersion liquid, paste, the product that can dust that directly can spray, send out material or granule form, through spraying, spray, dust, sprawl or watering and use.Type of service depends on the intention of expectation fully; Their intentions are guaranteed the fine distribution as much as possible according to active compound of the present invention under each situation.
Below be nonrestrictive instance preparaton:
1. the product of dilute with water.From the seed treatment agent intention, this kind product can be through dilution
Or not diluted be applied to seed.
A) the water dissolvable enriched material (SL, LS)
The active compound of 10 weight parts is dissolved in the water or the water-soluble solvent of 90 weight parts.As alternative, add wetting agent or other auxiliary agent.Active compound dissolves when dilute with water, obtains the preparaton of 10% (w/w) active compound this moment.
B) dispersible agent (DC)
The active compound of 20 weight parts is dissolved in the pimelinketone of 70 weight parts, and the dispersion agent that adds 10 weight parts is Vinylpyrrolidone polymer for example.Dilute with water provides dispersion liquid, obtains the preparaton of 20% (w/w) active compound this moment.
C) missible oil (EC)
The active compound of 15 weight parts is dissolved in the YLENE of 7 weight parts, adds calcium dodecylbenzene sulphonate and castor oil ethoxylate (5 weight parts under each situation).Dilute with water provides emulsion, obtains the preparaton of 15% (w/w) active compound this moment.
D) emulsion (EW, EO, ES)
The active compound of 25 weight parts is dissolved in the YLENE of 35 weight parts, adds calcium dodecylbenzene sulphonate and castor oil ethoxylate (5 weight parts under each situation).Through emulsification machinery (for example Ultraturrax) this mixture is introduced the water of 30 weight parts, and process the homogeneous emulsion.Dilute with water provides emulsion, obtains the preparaton of 25% (w/w) active compound this moment.
E) suspension-s (SC, OD, FS)
In the ball mill that stirs, pulverize the active compound of 20 weight parts, water or the organic solvent of dispersion agent, wetting agent and 70 weight parts that adds 10 weight parts is to obtain meticulous active compound suspension-s.Dilute with water provides the steady suspension of active compound, obtains the preparaton of 20% (w/w) active compound this moment.
F) water-dispersibility granula and water-soluble granular formulation (WG, SG)
Active compound through technical equipment (for example extrude, spray tower, fluidized-bed) fine grinding 50 weight parts adds the dispersion agent and the wetting agent of 50 weight parts, and processes water-dispersible or water-soluble granular formulation.Dilute with water provides the stable dispersion liquid or the solution of active compound, obtains the preparaton of 50% (w/w) active compound this moment.
G) water-dispersible powder and water-soluble powder (WP, SP, SS, WS)
Grind the active compound of 75 weight parts at the rotor-stator shredder, add dispersion agent, wetting agent and the silica gel of 25 weight parts.Dilute with water provides the stable dispersion liquid or the solution of active compound, obtains the preparaton of 75% (w/w) active compound this moment.
H) gel-preparaton (GF)
At the ball mill that stirs, pulverize the active compound of 20 weight parts, add the dispersion agent of 10 weight parts, the gelatinizing agent wetting agent of 1 weight part and the water of 70 weight parts or organic solvent are to obtain meticulous active compound suspension-s.Dilute with water provides the steady suspension of active compound, obtains the preparaton of 20% (w/w) active compound this moment.
2. be used for foliage applying not diluted the product used.For seed treatment intention, this kind product can through dilution or not diluted be applied to seed.
I) pulvis (DP, DS)
The active compound of fine grinding 5 weight parts mixes with the finely divided kaolin of 95 weight parts nearly.This provides the dusted product with 5% (w/w) active compound.
J) granule (GR, FG, GG, MG)
The active compound of fine grinding 0.5 weight part also merges with the carrier of 95.5 weight parts, obtains to have the preparaton of 0.5% (w/w) active compound this moment.Present method be extrude, spraying drying or fluidized-bed.This be provided for the blade face purposes not diluted the granule used.
K) ULV solution (UL)
The organic solvent that the active compound of 10 weight parts is dissolved in 90 weight parts is YLENE for example.This provides the product with 10% (w/w) active compound, with its not diluted use and be used for the blade face purposes.
Through adding water, moisture type of service can prepare from emulsion concentrates, paste or wettable powder (sprinkling property powder, oily dispersion liquid).In order to prepare emulsion, paste or oily dispersion liquid, can with former state be dissolved in oil or the material of solvent through wetting agent, tackifier, dispersion agent or emulsifying agent homogenize in water.Alternatively, can prepare enriched material, it comprise active substance, wetting agent, tackifier, dispersion agent or emulsifying agent and, if suitable, solvent or oil; And this kind enriched material is suitable for dilute with water.
Activity component concentration in the off-the-shelf can change in the wide region relatively.Generally speaking, scope is 0.0001 to 10%, preferred 0.01 to 1%.
Activeconstituents also can successfully use with ultralow-volume process (ULV), possibly use the preparaton that comprises the activeconstituents that surpasses 95 weight %, even use activeconstituents with need not additive.
Mixture
In the method for the invention; Formula I compound can with other activeconstituents, for example with other sterilant, insecticide; Weedicide; Fertilizer such as an ammonium nitrate, urea, potash and super phosphoric acid salt (superphosphate), plant poison and plant-growth regulator, safener and nematocides are used together.These other compositions can use in order or use with the above-mentioned compsn combination, if suitable also only before using, adding immediately (bucket mixes).For example, plant can be sprayed with the present composition before or after handling with other activeconstituents.
Can the sterilant of following tabulation M be used with compound according to the present invention, it possibly produce potential synergistic effect.It only is intended to illustrate possible combination, but is not that it is applied any restriction:
M.1. organic (sulfo-) phosphate compounds: orthene (acephate), azamethiphos (azamethiphos), azinphos ethyl (azinphos-ethyl), azinphos-methyl (az inphos-methyl), chlorethoxyfos (chlorethoxyfos); Chlorfenvinphos (chlorfenvinphos), chlormephos (chlormephos), chlopyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), Resistox (coumaphos); Cynock (cyanophos), demeton-methyl (demeton-S-methyl), diazinon (diazinon), DDVP (dichlorvos/DDVP); Carbicron (dicrotophos), Rogor (dimethoate), dimethylvinphos (dimethylvinphos), disulfoton (disulfoton); EPN (EPN), Ethodan (ethion), phonamiphos (ethoprophos), famphur (famphur); Fenamiphos (fenamiphos), fenifrothion (fenitrothion), Entex (fenthion), flupyrazophos; Lythidathion (fosthiazate), heptenophos (heptenophos), isoxathion (isoxathion), malathion (malathion); Afos (mecarbam), acephatemet (methamidophos), methidathion (methidathion), Menite (mevinphos); Azodrin (monocrotophos), 2-dichloroethylk dimethyl phosphate (naled), omethoate (omethoate), oxydemeton_methyl (oxydemeton-methyl); Parathion (parathion), parathion-methyl (parathion-methyl), phenthoate dimephenthoate cidial (phenthoate), thimet (phorate); Phosalone (phosalone), phosmet (phosmet), phosphamidon (phosphamidon), phoxim (phoxim); Pirimiphos-methyl (pirimiphos-methyl), Profenofos (profenofos), propetamphos (propetamphos), Toyodan (prothiofos); Pyraclofos (pyraclofos), pyridaphethione (pyridaphenthion), quinalphos (quinalphos), sulfotep (sulfotep); Butyl pyrimidine phosphorus (tebupirimfos), Temefos (temephos), Terbufos (terbufos), stirofos (tetrachlorvinphos); Thiometon (thiometon), Hostathion (triazophos), metrifonate (trichlorfon), vamidothion (vamidothion);
M.2. carbamate compounds: Aldicarb (aldicarb), alanycarb (alanycarb), Ficam (bendiocarb), Benfuracard micro (benfuracarb); Butocarboxim (butocarboxim), butanone sulfone prestige (butoxycarboxim), carbaryl (carbaryl), carbofuran (carbofuran); Carbosulfan (carbosulfan), ethiofencarb (ethiofencarb), Bassa (fenobucarb), Carzol (formetanate); Furathiocarb (furathiocarb), Mobucin (isoprocarb), methiocarb (methiocarb), Methomyl (methomyl); MTMC (metolcarb), oxamyl (oxamyl), Aphox (pirimicarb), arprocarb (propoxur); The two prestige (thiodicarb) of sulphur, thiofanox (thiofanox), Landrin (trimethacarb); XMC (XMC), Meobal (xylylcarb), triaguron (triazamate);
M.3. pyrethroid (pyrethroid) compound: acrinathrin (acrinathrin), allethrin (allethrin), d-cis-trans allethrin (allethrin), the trans allethrin of d-(allethrin); Bifenthrin (bifenthrin), bioallethrin (bioallethrin), S-bioallethrin (bioallethrin S-cylclopentenyl), bioresmethrin (bioresmethrin); Cycloprothrin (cycloprothrin), FCR-1272 (cyfluthrin), b-FCR-1272 (beta-cyfluthrin), cyhalothrin (cyhalothrin); Lambda-cyhalothrin (lambda-cyhalothrin), gamma-cyhalothrin (cyhalothrin), PP-383 (cypermethrin), a-PP-383 (alpha-cypermethrin); B-PP-383 (beta-cypermethrin), θ-PP-383 (theta-cypermethrin), ξ-PP-383 (zeta-cypermethrin); Cyphenothrin (cyphenothrin), Deltamethrin (deltamethrin), empenthrin (empenthrin); S-fenvalerate (esfenvalerate), ether chrysanthemum ester (etofenprox), Fenvalerate (fenpropathrin); Fenvalerate (fenvalerate), flucythrinate (flucythrinate), flumethrin (flumethrin); Taufluvalinate (tau-fluvalinate), halfenprox (halfenprox), alkynes miaow chrysanthemum ester (imiprothrin); Methoxy benzyl Flumethrin (metofluthrin), permethrin (permethrin), phenothrin (phenothrin); Prallethrin (prallethrin), profluthrin, pyrethrin (pyrethrin) (pyrethrin (pyrethrum)); Resmethrin (resmethrin), salifluofen (silafluofen), tefluthrin (tefluthrin); Tetramethrin (tetramethrin), tralomethrin (tralomethrin), transfluthrin (transfluthrin);
M.4. neotonin stand-in: hydroprene (hydroprene), kinoprene (kinoprene), methoprene (methoprene), fenoxycarb (fenoxycarb), pyrrole propyl ether (pyriproxyfen);
M.5. nicotinic acid receptor agonists/agonist compounds: acetamiprid (acetamiprid), bensultap (bensultap), cartap (cartap) hydrochloride; Thiophene worm amine (clothianidin), MTI-446 (dinotefuran), Provado (imidacloprid); Thiophene worm piperazine (thiamethoxam), Buddhist nun rattan pyrrole blue (nitenpyram), nicotine; Polyoxin (spinosad) (allosteric agonist), ethyl pleocidin (spinetoram) (allosteric agonist), thiophene worm quinoline (thiacloprid); Thiocyclam (thiocyclam), desinsection acid-sodium salt (thiosultap-sodium) and AKD1022.
M.6.GABA gated chloride channel antagonist compound: Niran (chlordane), 5a,6,9,9a-hexahydro-6,9-methano-2,4 (endosulfan), gamma-hch (lindane (lindane)); Second worm nitrile (ethiprole), fluorine worm nitrile (fipronil), pyrafluprole, pyriprole
M.7. chloride channel acvator: Avrmectin (abamectin), emamectin-benzoate (emamectin benzoate) is more visitd rhzomorph (milbemectin), lepimectin;
M.8.METI I compound: fenazaquin (fenazaquin), azoles mite ester (fenpyroximate), pyrimidifen (pyrimidifen); Pyridaben (pyridaben), tebufenpyrad (tebufenpyrad), azoles insect amide (tolfenpyrad); Flufenerim, tubatoxin (rotenone);
M.9.METI II and III compound: the mite quinone (acequinocyl) that goes out, fluacyprim, hydramethylnon (hydramethylnon);
M.10. the uncoupling agents of phosphorus oxide acidylate: bromothalonil (chlorfenapyr), DNOC (DNOC);
M.11. the suppressor factor of phosphorus oxide acidylate: azocyclotin (azocyclotin), cyhexatin (cyhexatin), butyl ether urea (diafenthiuron), fenbutatin oxide (fenbutatin oxide), alkynes mite special (propargite), tetradifon (tetradifon);
M.12. the disrupting agent of casting off a skin: cyromazine (cyromazine), ring worm hydrazides (chromafenozide), chlorine worm hydrazides (halofenozide), methoxyfenozide (methoxyfenozide), worm hydrazides (tebufenozide);
M.13. synergistic agent: Piperonyl Butoxide (piperonyl butoxide), De-Green (tribufos);
M.14. sodium channel closing compound: indenes worm prestige (indoxacarb), metaflumizone (metaflumizone);
M.15. fumigant: monobromethane (methyl bromide), trichloronitromethane (chloropicrin) sulfuryl fluoride (sulfuryl fluoride);
M.16. selectivity blocker: the crylotie that ingests, pyrrole aphid ketone (pymetrozine), flonicamid (flonicamid);
M.17. mite class growth inhibitor (growth inhibitors): four mite piperazines (clofentezine), hexythiazox (hexythiazox), second mite azoles (etoxazole);
M.18. chitin synthesis inhibitors: PP618 (buprofezin), two three WL 115110s (bistrifluron), fluorine pyridine urea (chlorfluazuron); Diflubenzuron (diflubenzuron), flucycloxuron (flucycloxuron), WL 115110 (flufenoxuron); Fluorine bell urea (hexaflumuron), lufenuron (lufenuron), fluorine uride (novaluron); Noviflumuron (noviflumuron), fluorobenzene urea (teflubenzuron) kills bell urea (triflumuron);
M.19. lipid biosynthesis inhibitor: spiral shell mite ester (spirodiclofen), Spiromesifen (spiromesifen), spiral shell worm ethyl ester (spirotetramat);
M.20.Octapaminergic agonist: amitraz (amitraz);
M.21. Reynolds is decided (ryanodine) receptor modulators: Flubendiamide (flubendiamide) and phthalyl amine compound (R)-; (S)-3-chloro-N1-{2-methyl-4-[1; 2; 2,2-tetrafluoro-1-(trifluoromethyl) ethyl] phenyl }-N2-(1-methyl-2-methylsulfonyl ethyl) phthalamide (M21.1)
M.22. isoxazoline compounds: 4-[5-(3,5-two chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-base]-2-methyl-N-pyridine-2-ylmethyl-BM (M22.1),
4-[5-(3,5-two chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-base]-2-methyl-N-(2,2,2-three fluoro-ethyls)-BM (M22.2),
4-[5-(3,5-two chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-base]-2-methyl-N-[(2,2,2-three fluoro-ethylamino formyl radicals)-methyl]-BM (M22.3),
4-[5-(3,5-two chloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-base]-naphthalene-1-carboxylic acid [(2,2,2-three fluoro-ethylamino formyl radicals)-methyl]-acid amides (M22.4) and
4-[5-(3, the 5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole-3-bases]-N-[(methoxyimino) methyl]-2-methyl benzamide (M22.5);
M.23. anthranilic acid lactam compound: Rynaxypyr (chloranthraniliprole), cyanogen worm BM (cyantraniliprole),
5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carboxylic acid [4-cyanic acid-2-(1-cyclopropyl-ethylamino formyl radical)-6-methyl-phenyl]-acid amides (M23.1),
5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carboxylic acid [2-chloro-4-cyanic acid-6-(1-cyclopropyl-ethylamino formyl radical)-phenyl]-acid amides (M23.2),
5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carboxylic acid [2-bromo-4-cyanic acid-6-(1-cyclopropyl-ethylamino formyl radical)-phenyl]-acid amides (M23.3),
5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carboxylic acid [2-bromo-4-chloro-6-(1-cyclopropyl-ethylamino formyl radical)-phenyl]-acid amides (M23.4),
5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carboxylic acid [2,4-two chloro-6-(1-cyclopropyl-ethylamino formyl radical)-phenyl]-acid amides (M23.5),
5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carboxylic acid [4-chloro-2-(1-cyclopropyl-ethylamino formyl radical)-6-methyl-phenyl]-acid amides (M23.6),
N '-(2-{ [5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carbonyl]-amino }-5-chloro-3-methyl-benzoyl-)-hydrazine carboxylic acid's methyl esters (M23.7),
N '-(2-{ [5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carbonyl]-amino }-5-chloro-3-methyl-benzoyl-)-N '-methyl-hydrazine carboxylic acid's methyl esters (M23.8),
N '-(2-{ [5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carbonyl]-amino }-5-chloro-3-methyl-benzoyl-)-N, N '-dimethyl--hydrazine carboxylic acid's methyl esters (M23.9),
N '-(3,5-two bromo-2-{ [5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carbonyl]-amino }-benzoyl-)-hydrazine carboxylic acid's methyl esters (M23.10),
N '-(3,5-two bromo-2-{ [5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carbonyl]-amino }-benzoyl-)-N '-methyl-hydrazine carboxylic acid's methyl esters (M23.11) and
N '-(3,5-two bromo-2-{ [5-bromo-2-(3-chloro-pyridine-2-yl)-2H-pyrazoles-3-carbonyl]-amino }-benzoyl-)-N, N '-dimethyl--hydrazine carboxylic acid's methyl esters (M23.12);
M.24. Malononitrile compound: 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3,3,3-three fluoro-propyl group) propane dinitrile (CF
2H-CF
2-CF
2-CF
2-CH
2-C (CN)
2-CH
2-CH
2-CF
3) (M24.1) and 2-(2,2,3,3,4,4,5,5-octafluoro amyl group)-2-(3,3,4,4,4-five fluorine butyl)-propane dinitrile (CF
2H-CF
2-CF
2-CF
2-CH
2-C (CN)
2-CH
2-CH
2-CF
2-CF
3) (M24.2);
M.25. microbial destruction agent: Bacillus thuringiensis (Bacillus thuringiensis) subspecies Israelensi; Bacillus sphaericus (Bacilluss phaericus); Bacillus thuringiensis subsp.aizawai (Bacillus thuringiensis subsp.Aizawai); Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Tenebrionis;
M.26. amino furan ketone compound:
4-{ [(6-bromopyridine-3-yl) methyl] (2-fluoro ethyl) amino } furans-2 (5H)-ketone (M26.1),
4-{ [(6-fluorine pyridin-3-yl) methyl] (2,2-two fluoro ethyls) amino } furans-2 (5H)-ketone (M26.2),
4-{ [(2-chlorine 1,3-thiazoles-5-yl) methyl] (2-fluoro ethyl) amino } furans-2 (5H)-ketone (M26.3),
4-{ [(6-chloropyridine-3-yl) methyl] (2-fluoro ethyl) amino } furans-2 (5H)-ketone (M26.4),
4-{ [(6-chloropyridine-3-yl) methyl] (2,2-two fluoro ethyls) amino } furans-2 (5H)-ketone (M26.5),
4-{ [(6-chloro-5-fluorine pyridin-3-yl) methyl] (methyl) amino } furans-2 (5H)-ketone (M26.6),
4-{ [(5,6-dichloropyridine-3-yl) methyl] (2-fluoro ethyl) amino } furans-2 (5H)-ketone (M26.7),
4-{ [(6-chloro-5-fluorine pyridin-3-yl) methyl] (cyclopropyl) amino } furans-2 (5H)-ketone (M26.8),
4-{ [(6-chloropyridine-3-yl) methyl] (cyclopropyl) amino } furans-2 (5H)-ketone (M26.9) and
4-{ [(6-chloropyridine-3-yl) methyl] (methyl) amino } furans-2 (5H)-ketone (M26.10);
M.27. all cpds: aluminium phosphide, amidoflumet, benclothiaz, benzoximate (benzoximate), Bifenazate (bifenazat e); Borax (borax), bromopropylate (bromopropylate), prussiate, benzene nitrile pyrrole mite ester (cyenopyrafen), fourth fluorine mite ester (cyflumetofen); Chinomethionate (chinomethionate), kelthane (dicofol), fluoroacetate (ester), phosphuret-(t)ed hydrogen, pyridine worm ether (pyridalyl); Seven Flubendiamides (pyrifluquinazon), sulphur, organosulfur compound, winestone vomitive, fluorine pyridine worm amine nitrile (sulfoxaflor); N-R '-2,2-dihalo--1-R " ring-propane methane amide-2-(2,6-two chloro-α, α, α-three fluoro-p-tolyl) hydrazone or N-R '-2; 2-two (R ' ") propionic acid amide-2-(2,6-two chloro-α, α, α-three fluoro-p-tolyl)-hydrazone, wherein R ' is methyl or ethyl; Halogen is chlorine or bromine, and R " being hydrogen or methyl and R ' " is methyl or ethyl, 4-fourth-2-alkynyloxy base-6-(3,5-dimethyl--piperidines-1-yl)-2-fluoro-pyrimidine (M27.1)
Cyclopropaneacetic acid, 1,1 '-[(3S, 4R, 4aR, 6S, 6aS; 12R, 12aS, 12bS)-and 4-[[(2-cyclopropyl ethanoyl) oxygen base] methyl]-1,3,4,4a; 5,6,6a, 12,12a, 12b-decahydro-12-hydroxyl-4; 6a, 12b-trimethylammonium-11-oxo-9-(3-pyridyl)-2H, 11H-naphtho-[2,1-b] pyrans is [3,4-e] pyrans-3 also, 6-two bases] ester (M27.2) and
8-(2-cyclo propyl methoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazine-3-yl)-3-aza-bicyclo [3.2.1] octane (M27.3).
Group M be purchased the compound that can get can be referring to The Pesticide Manual, 13thEdition, British Crop Protection Council (2003) and other are open.
Lepimectin is known in Agro Project, PJB Publications Ltd, and No-vember 2004.Benclothiaz and preparation thereof have been described in EP-A1454621.Methidathion (Methidathion) and paraoxon (Paraoxon) and preparation thereof have been described in Farm Chemicals Handbook, and Volume 88, Meister Publishing Company, 2001.Metaflumizone (Metaflumizone) and preparation thereof have been described in EP-A1 462 456.Pyrrole fluorine sulphur phosphorus (Flupyrazofos) has been described in Pesticide Science 54,1988, p.237-243 with US 4822779.Pyrafluprole and preparation thereof have been described in JP 2002193709 and WO 01/00614.Pyriprole and preparation thereof have been described in WO 98/45274 and US 6335357.Amidoflumet and preparation thereof have been described in US 6221890 and JP 21010907.Flufenerim and preparation thereof have been described in WO 03/007717 and WO 03/007718.AKD 1022 and preparation thereof have been described in US 6300348.Rynaxypyr (chloranthraniliprole) has been described in WO 01/70671, WO 03/015519 and WO 05/118552.Cyanogen worm BM (Cyantranil iprole) has been described in WO 01/70671, WO 04/067528 and WO 05/118552.Anthranilic acid lactams M23.1 to M23.6 has been described in WO 2008/72743 and WO 200872783, and those M23.7 to M23.12 have described and WO2007/043677.Phthalamide M 21.1 is known in WO 2007/101540.Fourth fluorine mite ester (Cyflumetofen) and preparation thereof have been described in WO 04/080180.Amido quinazoline ketone compound seven Flubendiamides (Pyrifluquinazon) have been described in EP A 109 7932.Sulphur sulfoximide fluorine pyridine worm amine nitrile (Sulfoxaflor) has been described in WO 2006/060029 and WO 2007/149134.Alkynyl ether compound M27.1 is described in for example JP 2006131529.Organosulfur compound has been described in WO 2007060839.Isoxazoline compounds M 22.1 to M 22.5 has been described in for example WO2005/085216, WO 2007/079162 and WO 2007/026965.Amino furan ketone compound M 26.1 to M 26.10 has been described in for example WO 2007/115644.Pyripyropene verivate M 27.2 has been described in WO 2008/66153 and WO 2008/108491.Pyridazine compound M 27.3 has been described in JP 2008/115155.Those of Malononitrile compound (M24.1) and (M24.2) be described in WO 02/089579, WO 02/090320, and WO 02/090321, and WO 04/006677, and WO 05/068423, WO 05/068432 and WO 05/063694.
Mycocidal mixing companion is selected from down those that organize: acyl group alanine such as M 9834 (benalaxyl), metalaxyl (metalaxyl), ofurace (ofurace); Wakil (oxadixyl), amine derivative such as aldimorph, dodine (dodine); Dodemorph (dodemorph), butadiene morpholine (fenpropimorph), fenpropidin (fenpropidin); Guazatine acetate (guazatine), iminoctadine (iminoctadine), volution bacterium amine (spiroxamin); Tridemorph (tridemorph)
Anilino-pyrimidine such as phonetic mould amine (pyrimethanil); Mepanipyrim (mepanipyrim) or cyrodinyl, microbiotic such as cycloheximide (cycloheximid), grisovin (griseofulvin); Kasugamycin (kasugamycin); Myprozine (natamycin), polyoxin (polyoxin) or Streptomycin sulphate (streptomycin)
Azole such as bitertanol (bitertanol), bromoconazole, SN-108266 (cyproconazole), difenoconazole (difenoconazole); Alkene azoles alcohol (diniconazole), fluorine ring azoles (epoxiconazole), RH-7592 (fenbuconazole), fluquinconazole (fluquiconazole); Fluzilazol (flusilazole), own azoles alcohol (hexaconazole) presses down mould azoles (imazalil), metconazole (metconazole); Nitrile bacterium azoles (myclobutanil), Topaze (penconazole), Wocosin 50TK (propiconazole), prochloraz (prochloraz); Prothioconazoles (prothioconazole), tebuconazole (tebuconazole), triazolone (triadimefon), triadimenol (triadimenol); Fluorine bacterium azoles (triflumizol), triticonazole (triticonazole), flutriafol (flutriafol)
Dicarboximide class such as RP-26019 (iprodion), myclozolin (myclozolin), procymidone (procymidon), Vinclozoline (vinclozolin),
Dithiocarbamate(s) such as Karbam Black (ferbam), Parzate (nabam), MANEB 20WP (maneb); Zinc manganese ethylenebisdithiocarbamate (mancozeb), metamsodium (metam), Carbatene (metiram); Zinc 1,2-propylene bisdithiocarbamate (propineb), polycarbamate (polycarbamate), plug logical sequence (thiram); Ziram (ziram), zineb (zineb)
Heterogeneous ring compound such as anilazine (anilazine), F-1991 (benomyl), boscalid amine (boscalid), derosal (carbendazim); DCMO (carboxin), oxycarboxin (oxycarboxin), cyanogen frost azoles (cyazofamid), dazomet (dazomet); Dithianon (dithianon) , oxazole bacterium ketone (famoxadon), fenamidone (fenamidon), fenarimol (fenarimol); Fuberidazole (fuberidazole), fultolanil (flutolanil), furan pyrrole bacterium amine (furametpyr), isoprothiolane (isoprothiolane); SHA 458100 (mepronil), nuarimol (nuarimol), probenazole (probenazole), the third oxygen quinoline (proquinazid); Pyrifenox (pyrifenox), pyroquilon (pyroquilon), benzene oxygen quinoline (quinoxyfen), silicon metsulfovax (silthiofam); Thiabendazole (thiabendazole), thiophene fluorine bacterium amine (thifluzamid), thiophanate_methyl (thiophanate-methyl), tiadinil (tiadinil); Tricyclazole (tricyclazole), triforine (triforine)
Copper class mycocide such as Bordeaux mixture (bordeaux mixture), venus crystals, Cupravit (copper oxychloride), Basic Chrome Sulphate,
Nitrophenyl derivative such as Niagara 9044 (binapacryl), dinitrocrotonate (dinocap), dinobuton (dinobuton), nitrothalisopropyl,
Phenylpyrrole class such as fenpiclonil (fenpiclonil) or fludioxonil (fludioxonil),
Sulphur,
Other mycocide such as Acibenzolar (acibenzolar-S-methyl), benzene metsulfovax ester (benthiavalicarb), ring propionyl bacterium amine (carpropamid), m-tetrachlorophthalodinitrile (chlorothalonil); Ring fluorine benzyl acid amides (cyflufenamid), white urea cyanogen (cymoxanil), diclomezin (diclomezin), two chlorine zarilamids (diclocymet); The mould prestige of second (diethofencarb), edifenphos (edifenphos), Guardian (ethaboxam), fenhexamid (fenhexamid); Fentin (fentin)-acetate, rice blast acid amides (fenoxanil), ferimzone (ferimzone), PP-192 (fluazinam); Triethylphosphine acid (fosetyl), triethylphosphine acid (fosetyl)-aluminium salt, iprovalicarb (iprovalicarb); Perchlorobenzene (hexachlorobenzene), metrafenone (metrafenon), pencycuron (pencycuron); SN 39744 (propamocarb), phthalide (phthalide), tolclofosmethyl (toloclofos-methyl); Quintozene (quintozene), zoxamide (zoxamid)
Strobilurins class (strobilurins) is like ICIA 5504 (azoxystrobin); Ether bacterium amine (dimoxystrobin), fluoxastrobin (fluoxastrobin), BAS 490F (kresoxim-methyl); SSF 126 (metominostrobin); Orysastrobin (orysastrobin), ZEN 90160 (picoxystrobin) or oxime bacterium ester (trifloxystrobin)
Sulfenic acid verivate such as Difolatan (captafol), Vancide 89 (captan), dichlofluanid (dichlofluanid), Phaltan (folpet), Tolylfluanid (tolylfluanid),
Cinnemamides and analogue such as HSDB 6915 (dimethomorph), fluorine acyl bacterium amine (flumetover) or SYP-L190 (flumorph).
Use
Because the activity of their excellence, said formula I compound can be used to prevent and kill off animal pest.In view of the above; The present invention also provides the method for preventing and kill off animal pest; This method comprises insect, their food supply, their habitat or their breeding farm; Perhaps cultivated plant; Plant propagation material (like seed), insect soil, zone, material or the environment of growing and maybe can grow wherein, perhaps the desire protection in order to avoid insect is attacked or material, cultivated plant, plant propagation material (like seed), soil, surface or the space of infecting with the formula I compound or its salt of insecticidal effective dose or the compositions-treated that as above defines.
Preferably, the inventive method protective plant reproductive material (like seed) and from its growing plants in order to avoid animal pest attack or infect and comprise plant propagation material (like seed) is gone up acceptable salt with the formula I compound of the as above definition of insecticidal effective dose or its agricultural or with the Pestcidal compositions processing that defines like context of insecticidal effective dose.The inventive method is not limited to protect " substrate " (plant, plant propagation material, earth materials etc.) of having handled according to the present invention; It also has prophylactic effects; For example the protection growth is from the plant of treated plant propagation material (like seed), and this plant itself is not through handling.
In implication of the present invention, " animal pest " preferably is selected from arthropods and threadworms, more preferably harmful insect class, arachnids and threadworms, even more preferably insects, mite class and threadworms.
The present invention also provides the Pestcidal compositions of the above-mentioned animal pest of antagonism; If it comprises at least a formula I compound of the amount with insecticidal action or at least a tensio-active agent of its at least a agriculturally useful salt and at least a an inert liq and/or agronomically acceptable carrier of solid and hope.
This kind compsn can comprise single-activity formula I compound or its salt or according to the mixture of several active formula I compounds of the present invention or their salt.The mixture that can comprise each isomer or isomer mixture and each tautomer or tautomer according to compsn of the present invention.
Animal pest is insects, arachnids and threadworms, and plant, soil or plant-growth can contact through any application process as known in the art and formula I compound or the compsn that contains them in wherein water.At this point, " contact " comprise direct contact (said compound being applied directly on animal pest or the plant-typically being applied to leaf, stem or the root of plant) and indirect contact (said compound being applied to the location of animal pest or plant).
Can through plant/crop is contacted with the formula I compound of insecticidal effective dose with formula I compound or the insect-killing composition that comprises them protect growing plant and farm crop in order to avoid animal pest particularly insects, mite class or arachnids attack or infect.Term " crop " is meant farm crop and the farm crop of results in the growth.
The compounds of this invention is important especially with comprising in their many insects of compsn on preventing and kill off various cultivated plants, said various cultivated plants such as cereal class, root crop, oily section crop, vegetables, spice berry, ornamental plant, the for example seed of durum wheat and other wheat; Barley, oat, rye, corn (fodder maize and sugared corn/sweet corn and field corn), soybean, oily section crop, cress, cotton; Sunflower Receptacle, banana, rice, rape, turnip rape, beet, fodder beet; Eggplant, yam, gramineous grass, lawn, turf, feed-use grass, tomato; Leek, pumpkin (pumpkin)/pumpkin (squash), Caulis et Folium Brassicae capitatae, the iceberg lettuce, pepper, cucumber, melon; The rape plant, melon, beans, pea, garlic, onion, Radix Dauci Sativae; Tuberous plant such as yam, sugarcane, tobacco, grape, petunia, Herba Erodii/Flos Pelargonii, wild pansy and Flower of Garden Balsam.
The compounds of this invention former state or use with composition forms: through with insects or desire protection in order to avoid the plant of attack of insect, plant propagation material such as seed, soil, surface, material or room handle with the active compound that kills the insect significant quantity.This application can be in insect infection plant, plant propagation material such as seed, soil, surface, material or room before and carry out afterwards.
The present invention also comprises methods for combating animal pests; It comprises food supply, cultivated plant, seed, soil, zone, material or the environment that animal pest, their habitat, breeding farm, wherein said animal pest are being grown and maybe can grown, and perhaps desire protection is in order to avoid animal is attacked or material, plant, seed, soil, surface or the space of infecting contact with the mixture of at least a active formula I compound of insecticidal effective dose.
In addition, animal pest can be prevented and kill off through its food supply of target pest, habitat, breeding farm or its location are contacted with the formula I compound of insecticidal effective dose.At this point, this application can be carried out before or after insect infect the farm crop of location, growth farm crop or results.
Compound of the present invention can also prophylactically be applied to the place that there is insect in expection.
Formula I compound also can be used for protecting growing plants to avoid insect attacking or infect through plant is contacted with the formula I compound of insecticidal effective dose.Contact at this point, " " comprises direct contact (said compound being applied directly on insect and/or the plant-typically being applied to leaf, stem or the root of plant) and indirect contact (said compound being applied to the location of insect and/or plant).
" location " means habitat, breeding farm, plant, seed, soil, zone, material or the environment that insect wherein or parasite are being grown and maybe can grown.
Whole reproductive ability parts that term " plant propagation material " is interpreted as representing plant are like seed and the vegetalitas vegetable material such as cuttage and the stem tuber (for example yam) that can be used for plant propagation.They comprise seed, root, fruit, stem tuber, bulb, rhizome, shoot, other part of bud and plant.Can also comprise and treating after germinateing or at the seedling and the young plant of transplanting after soil is emerged.These plant propagation materials can use the plant protection compound to handle to prevention in plantation or in transplanting or before.
Term " cultivated plant " is interpreted as and comprises the plant of having modified through breeding, mutagenesis or genetically engineered.The plant of gene modification is a plant, and its genetic stocks is modified through the use recombinant DNA technology, and can not easily obtain through hybridization, sudden change or natural reorganization under natural surroundings through the genetic stocks of modifying like this.Typically, one or more gene integrations are gone into the special properties of the genetic stocks of gene improved plant with the improvement plant.This kind genetic modification also includes but not limited to transitional modification the behind the target of albumen (oligopeptides or polypeptide), for example through glycosylation or polymkeric substance addition such as prenylization, acetylize or farnesylation partly or peg moiety (Biotechnol Prog.2001 Jul-Aug for example; 17 (4): 720-8., Protein Eng Des Sel.2004 Jan; 17 (1): 57-66, Nat Protoc.2007; 2 (5): 1225-35., Curr Opin Chem Biol.2006 Oct; 10 (5): 487-91.Epub 2006 Aug 28., Biomaterials.2001 Mar; 22 (5): 405-17, Bioconjug Chem.2005 Jan-Feb; 16 (1): 113-21 discloses).
Term " cultivated plant " should be understood and also comprises as conventional breeding method or engineered result and made it to tolerate the plant of using the certain kinds weedicide, said weedicide such as hydroxyl-phenylpyruvic acid dioxygenase (HPPD) suppressor factor; Acetolactate synthase (ALS) suppressor factor, (referring to for example US 6,222,100, WO 01/82685, and WO 00/26390 like the alkylsulfonyl ureas; WO 97/41218, and WO 98/02526, and WO 98/02527, and WO 04/106529, and WO 05/20673, and WO 03/14357; WO 03/13225, and WO 03/14356, and WO 04/16073) or imidazolone type (referring to for example US 6,222,100, WO 01/82685; WO 00/26390, and WO 97/41218, and WO 98/02526, and WO 98/02527, and WO 04/106529; WO 05/20673, and WO 03/14357, and WO 03/13225, and WO 03/14356, and WO 04/16073); Enol acetonyl shikimic acid-3-phosphate synthase (EPSPS) suppressor factor is like Glyphosate 62 IPA Salt (glyphosate) (referring to for example WO 92/00377); Glutamine synthetase (GS) suppressor factor, like careless ammonium phosphine (glufosinate) (referring to for example EP-A-0242236, EP-A-242246) or oxynil weedicide (referring to for example US 5,559,024).Make total cultivated plant herbicide-tolerant through conventional breeding method (mutagenesis); For example Clearfield
summer sowing rape (Canola) tolerates imidazolone type, for example imazamox (imazamox).Make cultivated plant such as soybean, cotton, corn, beet and rape herbicide-tolerant such as Glyphosate 62 IPA Salt and careless ammonium phosphine with gene engineering method, wherein some can be purchased by trade(brand)name RoundupReady
(Glyphosate 62 IPA Salt) and LibertyLink
(careless ammonium phosphine).
Term " cultivated plant " should be understood and also comprises through using recombinant DNA technology to make it synthetic following plant: one or more insecticidal proteins particularly are known in those insecticidal proteins of bacterial spore Bacillaceae (Bacillus), particularly Bacillus thuringiensis; Like
-intracellular toxin; CryIA (b) for example, CryIA (c), CryIF; CryIF (a2); CryIIA (b), CryIIIA, CryIIIB (b1) or Cry9c; Vegetalitas insecticidal protein (VIP), VIP1 for example, VIP2, VIP3 or VIP3A; Settle down the insecticidal protein of the bacterium of threadworms, said bacterium is that for example polished rod shape Pseudomonas (photorhabdus spp.) or Xenorhabdus belong to (Xenorhabdus spp.); The toxin that animal produces is like scorpion toxin, spider venom, melittin or other insect-specificity neurotoxin; Mycetogenetic toxin, like the streptomycete toxin, phytohemagglutinin is like pea or barley Sugar receptors; Lectin; Proteinase inhibitor, like trypsin inhibitor, serpin, patatin, cystatin or antipain; Ribosome inactivating protein (RIP), like Ricin, corn-RIP, toxalbumin, soft melon albumen, Saponaria officinalis toxalbumin or red bryony toxalbumin; The steroide metabolic enzyme, like 3-hydroxy steroids oxydase, ecdysteroids-IDP-glycosyl-transferring enzyme, cholesterol oxidase, ecdysone suppressor factor or HMG-CoA-reductase enzyme; The ion channel blocking agent is like sodium or calcium channel blocker; Neotonin ester kinases; Diuretic hormone acceptor (helicokinin receptors); The stilben synthase, bibenzyl synthase, chitinase or LSD.In context of the present invention, these insecticidal proteins or toxin also should be expressly understood and be preceding toxin, hybridization albumen, truncated protein or modified protein.Hybridize proteic characteristic and be the albumen territory new combination (referring to, for example WO 02/015701).Other instance that this kind toxin maybe can synthesize the genetic engineering modified plant of this kind toxin is disclosed in for example EP-A 374 753, and WO 93/007278, and WO 95/34656, and EP-A 427 529, and EP-A 451 878, WO 03/018810 and WO 03/052073.The method that produces the plant of this kind gene modification is that those skilled in the art are generally known, and is described in the routine publication as mentioned above.These insecticidal proteins that are contained in the plant of gene modification provide protection in order to avoid the concrete harmful insect that divides into groups of arthropods for producing these proteic plants; Beetle (Coleoptera (Coleoptera)) particularly; The invasion and attack of fly (Diptera (Diptera)) and butterfly and moth class (lepidopteran (Lepidoptera)) and plant parasitic nematodes class (nematoda (Nematoda)).
Term " cultivated plant " should be understood and also comprises through using recombinant DNA technology to make it synthetic one or more albumen to increase the plant of those plants to the resistance or the tolerance of bacterium, virus or fungal pathogens.The proteic instance of this kind is so-called " pathogenesis-related proteins " (PR albumen; Referring to for example EP-A 0 392 225); Plant diseases resistant gene (for example potato growing kind; It is expressed the acting resistant gene of phytophthora infestans (Phytophthora infestans) derived from the wild Solanum bulbocastanum of Mexico) or T4-N,O-Diacetylmuramidase (for example can synthesize these proteic potato growing kinds, it has the resistance of directed toward bacteria like the raising of separating amylobacter (Erwinia amylvora)).The method that produces the plant of this kind gene modification is that those skilled in the art are generally known, and is described in the for example above-mentioned publication.
Term " cultivated plant " should be understood and also comprises through using recombinant DNA technology to make it synthetic one or more proteic plants; It increases throughput, and (the biological example amount is produced; Grain harvest; Starch content, oil-contg or protein content), to the tolerance of arid, salinity or other growth-restrictive circumstances factor or to the insect of those plants and the tolerance of fungi, bacterium or viral pathogen.
Term " cultivated plant " should be understood and also comprises through using recombinant DNA technology to make it to contain the plant of the internal substance or the new internal substance of the modification amount that particularly improves human or animal's nutrition, for example produces the oily section crop (for example Nexera
rape) of health-promoting property long-chain omega-fatty acid or undersaturated ω-9 lipid acid.
Term " cultivated plant " should be understood and also comprises through using recombinant DNA technology to make it to contain particularly to improve the modification amount internal substance that raw material produces or the plant of new internal substance, for example produces the yam (for example Amflora
yam) of the pulullan of raising amount.
Generally speaking; " insecticidal effective dose " means the amount of realization to the needed activeconstituents of observable effects of growth, and said observable effects comprises necrosis, death, retardance, prevents and remove, destroys or reduce organic existence of target and active effect.For the used all cpds/compsn of the present invention, insecticidal effective dose can change.The said compsn of insecticidal effective dose also changes according to underlying condition, like the insecticidal effect and the time length of hope, weather, target kind, location, mode of administration etc.
In soil treating or be applied under the situation of insect habitat or nest, the scope of the amount of activeconstituents is 0.0001 to 500g every 100m
2, preferred 0.001 to 20g every 100m
2
Conventional amount of application in the material protection is the every m of 0.01g to 1000g active compound for example
2Treated material, the preferred every m of 0.1g to 50g
2
The insecticidal mixtures that is used for impregnating material typically contains 0.001 to 95 weight %, preferred 0.1 to 45 weight %, more preferably at least a repellent and/or the insecticide of 1 to 25 weight %.
In order to be used to handle crop plants, the amount of application of activeconstituents of the present invention can be 0.1g to a 4000g per hectare, preferred 25g to 600g per hectare, more preferably 50g to 500g per hectare.
Formula I compound is all effective through contact (via soil, glass, wall, tester, carpet, plant part or animal part) and ingest (bait formulation or plant part).
Compound of the present invention can also be used to resist non-crop insect pest, like ant, termite, wasp, fly, mosquito, cricket or blattaria.In order to be used for resisting said non-crop pests, formula I compound preferably uses with the bait formulation compsn.
Bait formulation can be liquid, solid or semi-solid preparation (example gel).Solid bait can form the suitable different shape of respectively using and form for example particulate state, bulk, bar-shaped, plate-like.Can liquid bait be charged into various devices to guarantee suitable using, for example open containers, spraying plant, droplet source or evaporation source.Gel can be based on moisture or oleaginous base, and can be mixed with viscosity, moisture keeps or the special requisite of aging property aspect.
The bait formulation that adopts in the said compsn is such product, and it has enough magnetisms and eats it to lure insects such as ant, white ants, wasp, fly, mosquito, cricket etc. or blattaria.Can usually regulate magnetism with feed stimulant or sex information.For example; The food stimulus agent not exclusively is selected from animal and/or vegetable-protein (digested tankage, fish meal or blood meal, insect part, yolk); The fat of animal and/or plant origin and oily; Or organic monose, oligose or saccharan, particularly sucrose, lactose, fructose, glucose, glucose, starch, pectin or even concentrated molasses or honey.Fresh or the corrupt part of fruit, farm crop, plant, animal, insects or its specific part can also be served as the feed stimulant.The sex sexual attractant is known to be that insect is specific more.The information specific sketch is set forth in the document and is well known by persons skilled in the art.
In order to be used for the bait formulation compsn, the typical content of activeconstituents is 0.001 weight % to 15 weight %, the active compound of preferred 0.001 weight % to 5% weight %.
The aerosol of formula I compound (for example in spray tank), oil spray or pump formula sprays preparaton height are suitable for unprofessional user prevent and kill off insect pests such as fly, flea, tick, mosquito or blattaria.Aerosol formulations preferably includes active compound, solvent such as lower alcohols (for example methyl alcohol, ethanol, propyl alcohol, butanols), ketone (acetone for example; Methyl ethyl ketone), has the paraffinic hydrocarbon (for example kerosene) of about 50 to 250 ℃ of boiling ranges, N, N-Methyl pyrrolidone, methyl-sulphoxide, aromatic hydrocarbon such as toluene, YLENE; Water, other auxiliary agent like sorbitol monooleate, have the oleyl ethoxylate of 3-7mol oxyethane, fatty alcohol ethoxylate such as emulsifying agent; Spice oil such as ether oil, the ester of medium chain fatty acid and lower alcohol, aromatic carbonyl compounds, if suitable stablizer such as Sodium Benzoate, amphoterics; Rudimentary epoxide, three ethyl orthoformates and propelling agent if desired such as propane, butane, nitrogen; Pressurized air, dme, carbonic acid gas, Nitrous Oxide, the perhaps mixture of these gases.
It is not use propelling agent that the oil spray formulations is different from the aerosol formulations part.
In order to be used for spray composite, the content of activeconstituents is 0.001 to 80 weight %, preferred 0.01 to 50 weight % and 0.01 to 15 weight % most preferably.
Formula I compound and each compsn thereof can also be used for mosquito-repellent incense and stacte, combustion tube, vaporization plate or long-term vaporizer, and mothproofing paper, mothproof pad or other do not rely on the vaporizer system of heat.
Prevent and kill off method (for example malaria, singapore hemorrhagic fever and the yellow jack of insect-borne communicable disease with formula I compound and each compsn thereof; Lymph filaricide and leishmaniasis) also comprise and handle house and dwelling house surface, air spray and infiltration heavy curtain, tent, clothing, tester, fly trapping cage etc.Be used for being applied to the insecticidal mixtures preferred package contain mixtures of fiber, fabric, cloth, nonwoven fabric, Web materials or foil and canvas, this mixture comprises insecticide, optional repellent and at least a tackiness agent.Suitable repellent is N for example, the N-diethylammonium--BM (DEET), N; N-diethylammonium monoacetylaniline (DEPA), 1-(3-hexamethylene-1-base-carbonyl)-2-methyl piperine, (2-methylol cyclohexyl) acetate lactone; 2-ethyl-1,3-pinakon, Indalone (indalone); The new decyl amide of methyl (MNDA), the pyrethroid that is not used in insect control as (+/-)-3-allyl group-2-methyl-4-oxo ring penta-2-(+)-thiazolinyl-(+)-trans-chrysanthemum monocarboxylate (Es-bioallethrin), and derived from or the repellent that is equal to plant milk extract such as from plant such as spot skin eucalyptus (Eucalyptus maculata); Vitex rotundifolia (Vitex rotundifolia), Cymbopogan martinli, lemongrass (Cymbopogan citratus) (lemongrass); Andropogon nardus (Cymopogan nartdus) (lemongrass) De limonene; Oxymethoxyallylbenzene, (+)-Eucamalol (1), (-)-1-table-eucamalol or rough plant milk extract.Suitable tackiness agent is selected from the for example polymkeric substance and the multipolymer (like vinyl-acetic ester and tertiary ethylene carbonate (vinyl versatate)) of aliphatic acid vinyl ester; The vinylformic acid and the methacrylic ester of alcohol; Like Bing Xisuandingzhi, 2-ethylhexyl acrylate, and methyl acrylate; Monoene formula and the undersaturated hydrocarbon of diene formula such as vinylbenzene and aliphatic diolefin such as divinyl.
Infiltration heavy curtain and tester are generally accomplished through textile material being immersed insecticide emulsion or dispersion liquid or it being sprayed to net on the account.
Formula I compound and compsn thereof can be used for protecting wood materials such as tree, board fence, sleeper, etc.; And building is like dwelling house, auxiliary building, factory; And material of construction, furniture, leather, fiber, vinyl goods, electric wire and cable etc. avoid ant and/or termite infestation, and are used to prevent and kill off ant and termite avoids damaging farm crop or mankind's (for example under situation of insect house-breaking and communal facility).Formula I compound not only is applied to surrounding soil surface or uses under the floor soil with the protection wood materials; It can also be applied to concrete surface under woodwork such as the floor, the recessed post of wall, crossbeam, wood veneer, furniture etc.; Woodwork such as shaving board, half plate (half boards) etc. and vinyl goods such as coating electric wire; Vinyl sheet, thermal insulation material such as styrenic foams etc.Under situation about using with the antagonism ant infringement farm crop or the mankind, ant agent for preventing and eliminating of the present invention is applied to farm crop or surrounding soil, perhaps be applied directly to ant nest etc.
Seed treatment
Formula I compound also is suitable for handling seed avoids the plant that the particularly autochthonal insect pest invasion and attack of insect pest and protection obtained with the protection seed root and shoot to resist soil pests and blade face insect.
Root and shoot antagonism soil pests and blade face insect that formula I compound is protected seed to avoid the soil pests invasion and attack particularly usefully and protected the plant that is obtained.Root and the shoot of the plant that protection is obtained are preferred.More preferably protect the shoot of gained plant to avoid puncture and suck insect infestations, wherein protection is in order to avoid the Phytophthira invasion and attack are most preferred.
Therefore; The present invention includes the protection seed and avoid insect; The root and the shoot that particularly avoid soil insect invasion and attack and protection seedling avoid insect; The method that particularly avoids soil and blade face insect infestations, said method comprise to be sowed seed before and/or after vernalization, is contacting with compound of Formula I or its salt.Preferably so especially method; Wherein root of plant and shoot are able to protection, more preferably such method, and wherein the plant shoot is able to protection in order to avoid boring and suck the juice insect infestations; Most preferably such method, wherein the plant shoot is able to protection in order to avoid the Phytophthira invasion and attack.
The propagulum that the term seed is forgiven seed and all categories includes but not limited to, sexual seed is planted piece, root turion, and bulb, bulb, fruit, stem tuber, grain, cuttage, cut shoot etc., and in preferred embodiment, mean mictic.
The term seed treatment comprises all suitable seed treatment known in the art, as seed dressing, seed pelleting, seed dust, seed soaking and seed granulate.
The present invention also comprises and contains active compound or with the seed of its dressing.
Term " use ... dressing and/or contain " usually represent activeconstituents when using the overwhelming majority on the surface of breeding product, although depend in the application process composition that more or less part can penetrate the breeding product.Under the situation of said breeding product (again) plantation, it can the assimilating activity composition.
Suitable seed is following seed: cereal, root crop, oily section crop, vegetables, seasoning plant, ornamental plant, the seed of durum wheat and other wheat for example, barley, oat; Rye, corn (fodder maize and sugar are with corn/sweet corn and field corn), soybean, oily section crop, cress, cotton, Sunflower Receptacle, banana, rice; Rape, turnip rape, beet, fodder beet, eggplant, yam, gramineous grass, lawn; Turf, feed-use grass, tomato, leek, pumpkin (pumpkin)/pumpkin (squash), Caulis et Folium Brassicae capitatae, iceberg lettuce, pepper; Cucumber, melon, the rape plant, melon, beans, pea, garlic, onion; Radix Dauci Sativae, tuberous plant such as yam, sugarcane, tobacco, grape, petunia, Herba Erodii/Flos Pelargonii, wild pansy and Flower of Garden Balsam.
In addition, active compound also can be used for handling the seed from plant, and said seed is owing to comprise engineered breeding method and the effect of herbicide-tolerant or mycocide or insecticide.
For example, active compound can be used for handling the seed from plant, its under organize weedicide resistance arranged: sulfonylurea; Imidazolone type, and careless ammonium phosphine or Glyphosate 62 IPA Salt-sec.-propyl ammonium salt and similar activity material (referring to for example, EP-A-0242236; EP-A-242246) (WO 92/00377) (EP-A-0257993; U.S.Pat.No.5,013,659) or be used to handle the genetically modified crops plant; For example having to produce makes plant resist specific insect (EP-A-0142924, the cotton of thuringiensis bacillus toxin EP-A-0193259) (Bt toxin) ability.
In addition, active compound also can be used to handle from comparing with existing plant of plant and has through modifying the seed of characteristic, its can be for example through traditional breeding way and/or produce sudden change or recombination method produces.For example; Many situation have been described; It wherein is the genetically modified crops plant (WO 91/13972) that the intention recombinant modified crop plants (for example WO 92/11376, and WO 92/14827, and WO 91/19806) of synthetic starch in the modified plant or the lipid acid with modification are formed.
Using the seed treatment of active compound carries out through the sprinkling or the seed that dusts before plant seeding and before plant emerges.
To the useful especially compsn of seed treatment agent for example is:
The A solubility concentrate thing (SL, LS)
The D emulsion (EW, EO, ES)
E suspension-s (SC, OD, FS)
F water dispersible granule and water-soluble granular formulation (WG, SG)
G water-dispersible powder and water dissolvable pulvis (WP, SP, WS)
H gel-preparaton (GF)
The I pulvis (DP, DS)
Conventional seed treatment agent preparaton comprises for example suspension seed-coating agent FS, solution LS, and dry powder treatment agent DS is used for the water-dispersion pulvis WS that slurry is handled, water dissolvable pulvis SS and emulsion ES and EC and gel formulation GF.These preparatons can be applied to dilution or not diluted ground seed.To seed be applied in sowing before carry out, wherein be applied directly to seed or after presprouting of seeds, use.
In preferred embodiment, the FS preparaton is used for seed treatment.Typically, the FS preparaton can comprise the 1-800g/l activeconstituents, 1-200g/l tensio-active agent, 0 to 200g/l antithrombotics, 0 to 400g/l tackiness agent, 0 to 200g/l pigment and until 1 liter of solvent, preferably water.
The FS preparaton that is used for the preferred especially formula I compound of seed treatment comprises 0.1 to 80 weight % (1 to 800g/l) activeconstituents, at least a tensio-active agent of 0.1 to 20 weight % (1 to 200g/l), for example the dispersion reagent of the wetting agent of 0.05 to 5 weight % and 0.5 to 15 weight % usually; Until 20 weight %, 5 to 20% antithrombotics for example, 0 to 15 weight %; The for example pigment of 1 to 15 weight % and/or dyestuff, 0 to 40 weight %, the for example tackiness agent of 1 to 40 weight % (tackiness agent/adhesion agent); Randomly until 5 weight %; The thickening material of 0.1 to 5 weight % for example, randomly 0.1 to 2% skimmer and randomly preserving agent such as biocide, inhibitor etc.; The amount of 0.01 to 1 weight % for example, and until filler/vehicle of 100 weight %.
The seed treatment agent preparaton can comprise tackiness agent and tinting material randomly extraly.
Can add tackiness agent with improvement active material adhesion on seed after handling.Suitable tackiness agent is homopolymer and the multipolymer of epoxy alkane such as oxyethane or propylene oxide, Yodo Sol VC 400, Z 150PH; Vinylpyrrolidone polymer class and multipolymer thereof, vinyl-vinyl acetate copolymer, acrylate homopolymer and multipolymer; The Vilaterm amine, polyvinyl lactam class and polymine, polyose such as Mierocrystalline cellulose, methylcellulose gum and starch; Polyolefin homopolymer and multipolymer such as alkene/copolymer-maleic anhydride; Urethane, polyester, polystyrene homopolymer and multipolymer.
Randomly, tinting material also can be included in the preparaton.The suitable tinting material or the dyestuff that are used for the seed treatment agent preparaton are rhodamine Bs, the C.I. Pigment Red 112, and C.I. solvent red 1, pigment Blue 15: 4, pigment Blue 15: 3, pigment Blue 15: 2, pigment Blue 15: 1; Pigment blue 80, Pigment Yellow 73 1, pigment yellow 13, Pigment Red 112, pigment red 4 8:2, pigment red 4 8:1; Pigment red 57:1, Pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36; Pigment Green 7, Pigment white 6, bistre 25, alkaline purple 10, alkalescence purple 49, Xylene Red 51; Xylene Red 52, azogeramine 4, acid blue 9, acid yellow 23, alkali red 1:1 0, alkali red 1:1 08.
In seed treatment, the amount of application of said compound I generally is the every 100kg seed of 0.1g to 10kg, the preferred every 100kg seed of 1g to 5kg, the more preferably every 100kg seed of every 100kg seed, particularly 1g to 200g of 1g to 1000g.
Therefore, the invention still further relates to the seed that comprises like the agriculturally useful salt of formula I compound defined herein or I.The amount of compound I or its agriculturally useful salt generally is the every 100kg seed of 0.1g to 10kg, the preferred every 100kg seed of 1g to 5kg every 100kg seed, particularly 1g to 1000g.For specific farm crop such as lettuce, consumption can be higher.
Animal health is used
Formula I compound or its enantiomer or the acceptable salt of veterinary science also resist in the animal body and the parasite of body surface especially effectively.
Therefore, theme of the present invention also provides and prevents and kill off in the animal body and ectozoal novel method.Another purpose of the present invention provides safer animal sterilant.Another object of the present invention is the animal sterilant that the tool improved potency further is provided, and it can use with the dosage lower than existing sterilant.In addition, another object of the present invention provides the animal sterilant, and it provides the parasite effect of long-term retention.
The invention still further relates to the formula I compound that contains the parasiticide significant quantity or the compsn of its enantiomer or acceptable salt of veterinary science and acceptable carrier, be used to resist in the animal body and ectozoa.
The present invention also is provided for handling, prevent and kill off, preventing and watches for animals resisting the method for parasite infestation and infection; It comprises per os, partly or use in the stomach other places or use one or more formulas I compound of parasiticide significant quantity to animal; Or its enantiomer or the acceptable salt of veterinary science, or comprise said compound compositions.
The present invention also is provided for handling, prevent and kill off, preventing and watches for animals resisting the non-therapeutic method of parasite infestation and infection, and it comprises the compsn of using formula I compound or its enantiomer or the acceptable salt of veterinary science of parasiticide significant quantity or comprising it to the location.
In another embodiment; The present invention is provided for resisting in the animal body and ectozoal compsn; It comprises one or more formulas I compound of parasiticide significant quantity, or its enantiomer or the acceptable salt of veterinary science, and one or more other promoting agent and acceptable carriers.The present invention also is provided for handling, prevent and kill off, preventing and watches for animals resisting the method for parasite infestation and infection, and it comprises one or more formulas I compound and other promoting agent of using significant quantity.
The present invention also provides preparation to be used to handle, prevent and kill off, prevent or the method for compositions of watch for animals antagonism parasite infestation or infection, and it comprises the formula I compound of parasiticide significant quantity or its enantiomer or the acceptable salt of veterinary science are included in the compsn that comprises it.
The invention still further relates to formula I compound is used to handle, prevent and kill off, prevent or watches for animals resist the purposes of parasite infestation or infection.
The compsn that the invention still further relates to formula I compound or comprise it is used to prepare the purposes of therapeutic treatment animal to the antiparasitic medicine that infects or attack.
The activity of the insect of compound antagonism agricultural do not show they prevent and kill off in the animal body with body surface in ectozoic suitability, the said for example low non-emetic dosage under Orally administered situation of preventing and kill off is with the metabolism consistency of animal, hypotoxicity, safe handling.In addition, those skilled in the art should understand, be used for resisting in the animal body with ectozoal situation under, the absorption of The compounds of this invention, distribution, metabolism and elimination are uncertain based on the validity of said compound in agricultural application.
Astoundingly, discoverable type I compound resists in the animal body and the interior epizoa of body surface effectively now.
Formula I compound or its enantiomer or the acceptable salt of veterinary science are preferred for preventing and kill off and prevent to infect with infection animal with the compsn that comprises them and comprises warm-blooded animal (comprising the mankind), bird and fish.For example; They are suitable for preventing and kill off and prevent Mammals such as ox, sheep, pig, camel, deer, horse, pig, poultry, rabbit, goat, dog and cat, buffalo, donkey, fawn and reinder; And fur coat is with animal such as mink, chinchilla and racoon, birds such as chicken, goose, turkey and duck, and fish such as fresh-water fishes and saltwater fish; Like trout, carp and eel, in infect and infect.
Formula I compound or its enantiomer or the acceptable salt of veterinary science are preferably used for preventing and kill off and prevent to infect with infection animal with the compsn that comprises them and comprises warm-blooded animal (getting rid of human), bird and fish.For example, they are suitable for preventing and kill off and prevent that mammiferous except that the mankind from infecting and infecting.
Formula I compound or its enantiomer or the acceptable salt of veterinary science are preferred for preventing and kill off and preventing infecting and infecting in domestic animal such as dog or the cat with the compsn that comprises them.
Invasion biology in warm-blooded animal and the fish includes but not limited to lice, stings lice, tick, and the nose bott, ked stings fly, housefly, fly, fly maggot, trombiculid, buffalo gnat, mosquito and flea.
Formula I compound or its enantiomer or the acceptable salt of veterinary science with comprise their the internal absorption of compsn and/or non-internal-absorting is prevented and kill off external source and/or entozoa is effective.They have activity to whole or some stage of growing.
Formula I compound is particularly usefully to external parasite resistance.In handling the ectozoic various embodiments of antagonism, said epizoa is one or more insects or spider, comprises Ctenocephalus (Ctenocephalides), Rh (Rhipicephalus); Dermacentor (Dermacentor), hard tick belongs to (Ixodes), Boophilus (Boophilus), Amblyomma (Ambylomma); Haemaphysalis (Haemaphysalis), Hyalomma (Hyalomma), itch mite belongs to (Sarcoptes), and the scabies mite belongs to (Psoroptes); Notoedres (Otodectes), Psoroptes (Chorioptes), Hypoderma (Hypoderma); Damalinia (Damalinia), Linognathus (Linognathus), Haematopinus (Haematopinus); Solenoptes, Trichodectes (Trichodectes), and Felicola (Felicola).Treated epizoa includes but not limited to flea, tick, mite, mosquito, fly, lice, calliphorid and combination thereof.
Formula I compound resists entozoa particularly usefully.Formula I compound comprises worm such as Anaplocephala (Anaplocephala), Ancylostoma (Ancylostoma), Anecator, Ascaris (Ascaris) to its active entozoa; Hepaticola (Capillaria), Cooperia (Cooperia), Diplopylidium (Dipylidium), Dirofilaria (Dirofilaria); Echinococcus (Echinococcus), Enterobius (Enterobius), fluke belongs to (Fasciola); Haemonchus (Haemonchus), Oesophagostumum, oersted Turbatrix (Ostertagia); Belascaris (Toxocara), Strongyloides (Strongyloides), Toxascaris (Toxascaris); Trichinella (Trichinella), Trichocephalus (Trichuris), and trichostrongylus (Trichostrongylus).
Formula I compound resists following parasite particularly usefully respectively:
Isopoda (Isopoda), for example damp worm (Oniscus asellus), Armadillidium vulgare and pillworm (Porcellio scaber);
Chilopoda (Chilopoda), for example Geophilus carpophagus and common house centipede belong to (Scutigera spp.);
Symphyla (Symphyla), for example kahikatea worm (Scutigerella immaculata);
Collembola (Collembola) is for example equiped with arms Onychiurus arcticus (Onychiurus arcticus belongs to (Onychiurus) armatus);
Hymenoptera (Hymenoptera), for example pine sawfoy belongs to (Diprion spp.), real tenthredinidae (Hoplocampa spp.), the hair ant belongs to (Lasius spp.), MonomoriumMayr (Monomorium pharaonis) and Vespa (Vespa spp.);
Bivalva, for example, the decorations shellfish belongs to (Dreissena spp.);
Coleoptera (Coleoptera), for example, acanthoscelides obtectus (Acanthoscelides obtectus), the beak rutelian belongs to (Adoretus spp.); Blue hair stern firefly chrysomelid (Agelastica alni), click beetle belongs to (Agriotes spp.), yam gill cockchafer (Amphimallon solstitialis), furniture death watch beetle (Anobium punctatum); Longicorn beetle belongs to (Anoplophora spp.), and flower resembles genus (Anthonomus spp.), Anthrenus (Anthrenus spp.), and Ah gill cockchafer belongs to (Apogonia spp.); Latent food first belongs to (Atomaria spp.), moth-eaten belong to (the Attagenus spp.) of fur, and Bruchidius obtectus, bean weevil belongs to (Bruchus spp.); Tortoise resembles genus (Ceuthorhynchus spp.), Bei Wei Aralia curculionid (Cleonus mendicus), and wide chest click beetle belongs to (Conoderus spp.), and collar resembles genus (Cosmopolites spp.); The brown nz rib wing melolonthid (Costelytra zealandica), Curculio (Curculio spp.), the latent beak of Yang Gan resembles (Cryptorhynchus lapathi), and khapra beetle belongs to (Dermestes spp.); Chrysomelid genus (Diabrotica spp.), epilachna genus (Epilachna spp.), Faustinus cubae, globose spider beetle (Gibbium psylloides); Black different pawl sugarcane cockchafer (Heteronychus arator), Hylamorpha elegans, North America house longhorn beetle (Hylotrupes bajulus), alfalfa leaf resembles (Hypera postica); Brown bark beetle belongs to (Hypothenemus spp.), the big brown hock gill cockchafer of sugarcane (Lachnosterna consanguinea), and colorado potato beetles (Leptinotarsa decemlineata), rice water resembles (Lissorhoptrus oryzophilus); The tube beak resembles genus (Lixus spp.), the moth-eaten genus of powder (Lyctus spp.), Meligethes aeneus, gill cockchafer in May (Melolontha melolontha); Migdolus spp., China ink day Bos (Monochamus spp.), Naupactus xanthographus, golden spider beetle (Niptus hololeucus); Coconut palm moth rhinoceros cockchafer (Oryctes rhinoceros), saw-toothed grain beetle (Oryzaephilus surinamensis), black grape ear image (Otiorrhynchus sulcatus), little blue and white cockchafer (Oxycetonia jucunda); Horseradish ape chrysomelid (Phaedon cochleariae), food phyllobranchia cockchafer belongs to (Phyllophaga spp.), Japan popillia flavosellata fairmaire (Popillia japonica); Premnotrypes spp., rape golden head flea beetle (Psylliodes chrysocephala), Ptinus (Ptinus spp.); Dark-coloured ladybug (Rhizobius ventralis), lesser grain borer (Rhizopertha dominica), Sitophilus (Sitophilus spp.); Point Rhynchophorus (Sphenophorus spp.), stem resembles genus (Sternechus spp.), comprehensive order (Symphyletes spp.); Bloom first (Tenebrio molitor), Tribolium (Tribolium spp.), the spot khapra beetle belongs to (Trogoderma spp.); Seed resembles genus (Tychius spp.), and ridge tiger day Bos (Xylotrechus spp.) belongs to (Zabrus spp.) apart from ground beetle;
Flea class (Siphonaptera), ctenocephalides felis for example, ctenocephalides canis, Xanthopsyllacheopis and Ceratophyllus, Pulex irritans, chigo, and ceratophyllus fasciatus;
Blattaria (Blattodea (Blattaria)-Blattodea (Blattodea)), Groton bug (Blattella germanica) for example, Blattella asahinae; Periplaneta americana (Periplaneta americana); The big Lian (Periplaneta japan) of Japan, the big Lian of foxiness (Periplaneta brunnea), Peroplaneta fluligginosa (Periplaneta fuligginosa); Australian cockroach (Periplaneta australasiae), and oriental cockroach (Blatta orientalis);
Fly, mosquito (Diptera (Diptera)), Aedes (Aedes spp.) for example, like Aedes aegypti (Aedes aegypti), informal voucher yellow-fever mosquito (Aedes albopictus), Aedes vexans (Aedes vexans); Mexico is by trypetid (Anastrepha ludens), and Anopheles (Anopheles) is such as anopheles maculipennis (Anopheles maculipennis), garden march fly (Bibio hortulanus), Anopheles crucians, Anopheles albimanus; Anopheles costalis (Anopheles gambiae), Anopheles freeborni, Anopheles leucosphyrus, anopheles minius (Anopheles minimus), anopheles quadrimaculatus (Anopheles quadrimaculatus); Calliphora erythrocephala, calliphora erythrocephala (Calliphora vicina), maggot disease gold fly (Chrysomya bezziana), Chrysomya hominivorax, Chrysomya macellaria; Chrysops discalis, Chrysops silacea, Chrysops atlanticus, cochliomyia bominovorax of Callitroga (Cochliomyia spp.) (Cochliomyia hominivorax), cordylobia anthropophaga (Cordylobia anthropo-phaga); Culicoides furens, Culex (Culex spp.) is like northern house (Culex pipiens), Culex nigripalpus, Culex quinquefasciatus (Culex quinquefascia-tus), Culex tarsalis; Culiseta inornata, Culiseta melanura, human botfly (Dermatobia homini s), Fannia (Fannia spp.) is like Fannia canicularis (Fannia canicularis), Gasterophilus intestinalis (Gasterophilus intestinalis); Glossina morsitans (Glossina morsitans), glossina palpalis (Glossina palpalis), brown sufficient tsetse fly (Glossina fuscipes) is intended and posts tsetse fly (Glossina tachinoides), west horn fly (Haematobia irritans); Saddle cecidomyiia (Haplodiplosis equestris), Hippelates spp., Hypoderma (Hypoderma spp.) be like Hypoderma lineata, Leptoconops torrens; Lucilia caprina, Lucilia (Lucilia spp.) be like lucilia cuprina (Lucilia cuprina), lucilia sericata (Lucilia sericata), Lycoria pectoralis; Mansonia (Mansonia spp.), Musca (Musca spp.) be like housefly (Musca domestica), false stable fly (Muscina stabulans), and Oestrus (Oestrus spp.) is like Oestrus ovis (Oestrus ovis); Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum; Sarcophaga haemorrhoidalis, Sarcophaga (Sarcophaga sp.), Simulium vittatum, Genus Stomoxys (Stomoxys spp.) is like tatukira (Stomoxys calcitrans); Gadfly (Tabanus spp.) is as having a liking for the gadfly (Tabanus bovinus), Tabanus atratus, Tabanus lineola, Tabanus similis; Mediterranean fruitfly (Ceratitis capi-tata), Carysomyia (Chrysomyia spp.), Cuterebra (Cuterebra spp.), Fructus oleae europaeae fruit fly (Dacus oleae); Drosophila (Drosophila spp.), Gasterophilus (Gastrophilus spp.), Hylemyia (Hylemyia spp.), Hippobosca (Hyppobosca spp.); Liriomyza bryoniae belongs to (Liriomyza spp.), Bemisia spp (Nezara spp.), Oscinella frit (Oscinella frit), spinach spring fly (Pegomyia hyoscyami); Grass Hylemyia (Phorbia spp.), Tannia spp., European daddy-longlegs (Tipula paludosa), Wohlfahrtia (Wohlfahrtia spp.);
Gastropoda (Gastropoda), for example, A Yong Limax (Arion spp.); Biomphalaria (Biomphalaria spp.), Bulinus (Bulinus spp.), Limax (Deroceras spp.); The soil snail belongs to (Galba spp.); Lymnaea (Lymnaea spp.), Katayama (Oncomelania spp.), amber spiro spp (Succinea spp.);
Hemiptera (Heteroptera), for example, squash bug (Anasa tristis) is intended beautiful stinkbug and belongs to (Antestiopsis spp.); The soil chinch bug belongs to (Blissus spp.), and pretty fleahopper belongs to (Calocoris spp.), Campylomma livida, and different back of the body chinch bug belongs to (Cavelerius spp.); Cimex (Cimex spp.), Creontiades dilutus, Dasynus piperis, Dichelops furcatus; Pepper lace bug (Diconocoris hewetti), red cotton bug belongs to (Dysdercus spp.), and the America stinkbug belongs to (Euschistus spp.), and Eurygasterspp belongs to (Eurygaster spp.); Heliopeltis spp., Horcias nobilellus, Leptocorisa spp belongs to (Leptocorisa spp.), cotton boll beak coried (Leptoglossus phyl-lopus); Lygus bug belongs to (Lygus spp.), Macropes excavatus, Miridae (Miridae), Bemisia spp (Nezara spp.); Oebalus spp., Pentomidae, square butt stinkbug (Piesma quadrata), the wall stinkbug belongs to (Piezodorus spp.); Cotton fleahopper (Psallus seriatus), Pseudacysta persea, Rhodnius (Rhodnius spp.), Sahlbergella singularis (Sahlbergella singularis); Black stinkbug belongs to (Scotinophora) spp., pear crown network pentatomidae (Stephanitis nashi), Tibraca spp., vertebra Reduvius (Triatoma spp.);
Lice (Anoplura (Phthiraptera)), Damalinia (Damalinia spp.) for example, Haematopinus (Haematopinus spp.); Linognathus (Linognathus spp.), Pediculus (Pediculus spp.), Trichodectes (Trichodectes spp.); Head louse (Pediculus humanus capitis), Pediculus humanus corporis, Pthirus pubis; Haematopinus eurysternus (Haematopinus eurysternus); Haematopinus suis (Haematopinus suis), Linognathus vituli (Linognathus vituli), Bovicola bovis; Menopon gallinae, chick poultry louse (Menacanthus stramineus) and ox pipe lice (Solenopotes ca-pillatus);
Tick and parasitic mite (Parasitiformes (Parasitiformes)): tick (Ixodida); Ixodes scapularis, ixodes holocyclus (Ixodes holocyclus), Ixodes pacificus; Brown dog tick (Rhiphicephalus sanguineus); Dermacentor andersoni (Dermacentor andersoni), Dermacentor variabilis (Dermacentor variabilis), lone star tick (Amblyomma americanum); Spot flower tick (Ambryomma maculatum) is arranged; Ornithodorus hermsi, Ornithodorus turicata and parasitic mite (Mesostigmata (Mesostigmata)), for example ornithonyssus bacoti (Ornithonyssus bacoti) and Dermanyssus gallinae (Dermanyssus gallinae);
Spoke mite suborder (Actinedida) (preceding valve suborder (Prostigmata)) and flour mite order (Acaridida) (Astigmata (Astigmata)) for example honeybee tarsonemid mite belong to (Acarapis spp.), Cheyletiella (Cheyletiella spp.), and fowl chela li mite belongs to (Ornithocheyletia spp.); Myobia (Myobia spp.), Psorergates (Psorergates spp.), Demodex (Demodex spp.); Trombidium (Trombicula spp.), the yak mite belongs to (Listrophorus spp.), Tyroglyphus (Acarus spp.); Tyrophagus (Tyrophagus spp.) is had a liking for wooden mite and is belonged to (Caloglyphus spp.), and mite belongs to (Hypodectes spp.) under the neck; The wing mite belongs to (Pterolichus spp.), and the scabies mite belongs to (Psoroptes spp.), Psoroptes (Chorioptes spp.); Notoedres (Otodectesspp.); Itch mite belongs to (Sarcoptes spp.), and the scab mite belongs to (Notoedres spp.), and the lump mite belongs to (Knemidocoptes spp.); Cytoleichus (Cytodites spp.) and epithelium mite belong to (Laminosioptes spp);
Arachnida (Arachnida), for example, Acarus siro (Acarus siro), oranges and tangerines aceria (Aceria sheldoni); Peronium Eriophyes (Aculops spp.), acupuncture Eriophyes (Aculus spp.), Amblyomma (Amblyomma spp.), Argas (Argas spp.); Boophilus (Boophilus spp.), short whisker Acarapis (Brevipalpus spp.), Bryobia praetiosa (Bryobia praetiosa), Psoroptes (Chorioptes spp.); Dermanyssus gallinae (Dermanyssus gallinae), beginning Tetranychus (Eotetranychus spp.), goitre mite on the pears (Epitrimerus pyri); True Tetranychus (Eutetranychus spp.), Eriophyes (Eriophyes spp.), half tarsonemid mite belongs to (Hemitarsonemus spp.); Hyalomma (Hyalomma spp.), hard tick belongs to (Ixodes spp.), erythema spider (Latrodectus mactans); Metatetranychus spp., the unguiculus mite belongs to (Oligonychus spp.), Ornithodoros (Ornithodoros spp.); Panonychus citri belongs to (Panonychus spp.), oranges and tangerines wrinkle leaf Aculus (oranges and tangerines wrinkle leaf Aculus (Phyllocoptruta oleivora)), Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus); The scabies mite belongs to (Psoroptes spp.), Rh (Rhipicephalus spp.), Rhizoglyphus (Rhizoglyphus spp.); Itch mite belongs to (Sarcoptes spp.), Middle East gold scorpion (Scorpio maurus), Stenotarsonemus spp.; Tarsonemid mite belongs to (Tarsonemus spp.), Tetranychus (Tetranychus spp.), and tomato tiltedly carries on the back aceria (Vasates lycopersici);
Bugs (Heteroptera (Heteropterida)): bed bug (Cimex lec-tularius); Cimex hemipterus (Cimex hemipterus); Reduvius senilis; Vertebra Reduvius (Triatoma spp.), Rhodnius (Rhodnius ssp.), the Panstrongylus (Panstrongylus ssp.) and the back of tooth are hunted stinkbug (Arilus critatus);
Anoplura (Anoplurida), Haematopinus (Haematopinus spp.) for example, Linognathus (Linognathus spp.), Pediculus (Pediculus spp.), Pthirus (Phtirus spp.) and pipe lice belong to (Solenopotes spp);
Mallophaga (Mallophagida) (suborder Arnblycerina and Ischnocerina), for example the hair Trichodectes (Trimenopon spp.), Menopon spp.; Huge Trichodectes (Trinoton spp.); Bovicola (Bovicola spp.), Werneckiella spp., Lepikentron spp.; Trichodectes (Trichodectes spp.), and Felicola (Felicola spp);
Nematode (roundworms) nematoda (Nematoda):
Whipworm and Trichinosis (Trichosyringida); For example Trichinellidae (Trichinellidae) (Trichinella (Trichinella spp.)) is like trichina(Trichinella spiralis) (Trichinella spiralis); Trichinella nativa; Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis; (Trichocephalidae (Trichuridae)) Trichocephalus (Trichuris spp.) is like Trichuris trichuria, Hepaticola (Capillaria spp);
Rhabditis axei order (Rhabditida), Rhabditis (Rhabditis spp) for example, Strongyloides (Strongyloides spp.), Helicephalobus spp;
Strongylida, Strongylus (Strongylus spp.) for example, Ancylostoma (Ancylostoma spp.), Necator americanus; Bunostomum (Bunostomum spp.) (Ancylostoma), trichostrongylus (Trichostrongylus spp.), haemonchus (Haemonchus spp.) is like haemonchus contortus (Haemonchus contortus); Oersted Turbatrix (Ostertagia spp.), Cooperia (Cooperia spp.), Nematodirus (Nematodirus spp.); Dictyocaulus (Dictyocaulus spp.), Cyathostoma spp., oesophagostomum (Oesophagostomum spp.); Stephanurus dentatus, Ollulanus spp., Xia Baite Turbatrix (Chabertia spp.); Stephanurus dentatus, Syngamus trachea, Ancylostoma (Ancylostoma spp.); Ancylostoma (Uncinaria spp.), Globocephalus (Globocephalus spp.), Necator (Necator spp.); Metastrongylus (Metastrongylus spp.), Muellerius capillaris, Protostrongylus (Protostrongylus spp.); Angiostrongylus spp., Parelaphostrongylus spp.Aleurostrongylus abstrusus and Dioctophyma renale;
The worm guiding principle, for example, Ancylostoma duodenale (Ancylostoma duodenale), Ancylostoma ceylanicum; Acylostoma braziliensis, dictyocaulus filaria (Dictyocaulus filaria), bothriocephalus cordatus (Diphyllobothrium latum); Echinococcus granulosus (Echinococcus granulosus), Echinococcus multilocularis, Heterakis (Heterakis spp.); Hymenolepis nana (Hymenolepis nana), Hyostrongulus spp., sieve Ah nematode (Loa loa); Opisthorchis (Opisthorchis spp.), filaria volvulus (Onchocerca volvulus), Schistosomen spp.; Strongyloides fuelleborni, strongyloides intestinalis (Strongyloides stercoralis), Stronyloides spp.; Taeniasis bovis (Taenia saginata), taeniasis suis (Taenia solium), trichostrongylus (Trichostrongylus spp.);
Homoptera (Homoptera) for example, does not have net long tube Aphis (Acyrthosiphon spp.), Aeneolamia spp., and Agonoscena spp., Aleyrodes (Aleurodes spp.), sugarcane split aleyrodid (Aleurolobus barodensis); Aleyrodes (Aleurothrixus spp.) , Mango fruit leafhopper belongs to (Amrasca spp.), welted thistle short-tail aphid (Anuraphis cardui), and the kidney Aspidiotus belongs to (Aonidiella spp.), the short aphid of pears (Aphanostigma piri), Aphis (Aphis spp.); Grape leafhopper (Arboridia apicalis), the roundlet armored scale belongs to (Aspidiella spp.), and Aspidiotus belongs to (Aspidiotus spp.), and Atanus spp., potato ditch do not have net aphid (Aulacorthum solani), Aleyrodes (Bemisia spp.); Lee's short-tail aphid (Brachycaudus helichrysii), Brachycolus spp., brevicoryne brassicae (Brevicoryne brassicae), little brown back rice plant hopper (Calligypona marginata), Carneocephala fulgida, cane powder angle aphid (Ceratovacuna lanigera); Cercopidae (Cercopidae), lecanium belongs to (Ceroplastes spp.), knurl nail hair aphid (Chaetosiphon fragaefolii) in the strawberry, Chionaspis tegalensis, tea green leafhopper (Chlorita onukii), walnut blackspot aphid (Chromaphis juglandicola); Brown Aspidiotus belongs to (Chrysomphalus ficus), corn leafhopper (Cicadulina mbila), and Coccomytilus halli, soft a red-spotted lizard belongs to (Coccus spp.), and the tea Fischer conceals knurl aphid (Cryptomyzus ribis), Dalbulus spp.; Aleyrodes (Dialeurodes spp.), tangerine Psylla spp (Diaphorina spp.) is carried on the back armored scale in vain and is belonged to (Diaspis spp.), and Doralis spp. carries out giant coccid and belongs to (Drosicha spp.), western rounded tail Aphis (Dysaphis spp.); The ash mealybug belongs to (Dysmicoccus spp.), and green jassids belongs to (Empoasca spp.), and woolly aphid belongs to (Eriosoma spp.), and Erythroneura spp belongs to (Erythroneura spp.), Euscelis bilobatus, coffee ground mealybug (Geococcus coffeae); Phony disease of peach poison leafhopper (Homalodisca coagulata), mealy plum aphid (Hyalopterus arundinis), icerya purchasi belongs to (Icerya spp.), and sheet angle leafhopper belongs to (Idiocerus spp.), and flat beak leafhopper belongs to (Idioscopus spp.), small brown rice planthopper (Laodelphax striatellus); The ball a red-spotted lizard belongs to (Lecanium spp.), lepidosaphes shimer (Lepidosaphes spp.), radish aphid (Lipaphi serysimi), long tube Aphis (Macrosiphum spp.), Mahanarva fimbriolata, sorghum aphid forest type (Melanaphis sacchari); Metcalfiella spp., wheat does not have the net aphid, the flat wing spot aphid (Monellia costalis) of black edge, Monelliopsis pecanis, tumor aphid genus (Myzus spp.), lettuce is patched up Macrosiphus spp; Rice green leafhopper belongs to (Nephotettix spp.), brown paddy plant hopper, Oncometopia spp., Orthezia praelonga, red bayberry edge aleyrodid (Parabemisia myricae), a potato Psylla spp (Paratrioza spp.); The sheet armored scale belongs to (Parlatoria spp.), and the goitre woolly aphid belongs to (Pemphigus spp.), popcorn wing plant hopper (Peregrinus maidis), and continuous mealybug belongs to (Phenacoccus spp.), Yang Ping wing woolly aphid (Phloeomyzus passerinii), phorodon aphid (Phorodon humuli); Japan's Aphis (Phylloxera spp.), lily and armored scale (Pinnaspis aspidistrae), stern line mealybug belongs to (Planococcus spp.), the former giant coccid of pyriform (Protopulvinaria pyriformis), white mulberry scale (Pseudaulacaspis pentagona), mealybug belongs to (Pseudococcus spp.); Psylla spp (Psylla spp.), tiny golden wasp belongs to (Pteromalus spp.), Pyrilla spp., the large bamboo hat with a conical crown and broad brim Aspidiotus belongs to (Quadraspidiotus spp.), Quesada gigas, flat thorn mealybug belongs to (Rastrococcus spp.); Rhopalosiphum (Rhopalosiphum spp.), black bourch belongs to (Saissetia spp.), Scaphoides titanus, green bugs (Schizaphis graminum), sago cycas thorn Aspidiotus (Selenaspidus articulatus), long clypeus plant hopper belongs to (Sogata spp.); White backed planthopper (Sogatella furcifera), rice hopper belongs to (Sogatodes spp.), three horned frogs (Stictocephala festina), Tenalaphara malayensis, U.S.'s walnut deceive aphid (Tinocallis caryaefoliae), and wide chest froghopper belongs to (Tomaspis spp.); Sound Aphis (Toxoptera spp.), greenhouse whitefly (Trialeurodes vaporariorum), individual Psylla spp (Trioza spp.), jassids belongs to (Typhlocyba spp.), and sharp armored scale belongs to (Unaspis spp.), grape phylloxera (Viteus vitifolii);
Isoptera (Isoptera), for example, Reticulitermes (Reticulitermes spp.), odontotermes (Odontotermes spp.);
Lepidopteran (Lepidoptera), for example, Sang Jian Autographa spp (Acronicta major), tired noctuid (Aedia leucomelas); Ground Noctua (Agrotis spp.), Alabama argillacea does very Noctua (Anticarsia spp.), lopper worm (Barathra brassicae); Bucculatrix thurberiella, loose powder butterfly geometrid moth (Bupalus piniarius), yellow tail leaf roller (Cacoecia podana), Capua reticulana; Codling moth (Carpocapsa pomonella), orchard autumn geometrid moth (Cheimatobia brumata), straw borer spp (Chilo spp.), dragon spruce Choristoneura spp (Choristoneura fumiferana); Grape codling moth (Clysia ambiguella) (Clysia ambiguella), Cnaphalocerus spp., Egyptian noctuid (Earias insulana), the Anagasta kuehniella (Ephestia kuehniella) of boring; Pornography and drug moth (Euproctis chrysorrhoea) cuts Noctua (Euxoa spp.), Feltia spp., galleria mellonella waxmoth (Galleria mellonella); Helicoverpa spp., Heliothis (Heliothis spp.) is brownly knitted moth (Hofmannophila pseudospretella), tea long paper moth (Homona magnanima); Apple ermine moth (Hyponomeuta padella), greedy Noctua (Laphygma spp.), Lithocolletis blancardella; Green fruit winter noctuid (Lithophane antennata), Loxagrotis albicosta, Euproctis (Lymantria spp.); Malacosoma neustria (Malacosoma neustria), lopper worm (Mamestra brassicae), Mocisrepanda; Mythimna separata, Oria spp., Oulema oryzae (Oulema oryzae); Small noctuid (Panolis flammea), pink bollworm (Pectinophora gossypiella), oranges and tangerines leaf lyonetid (Phyllocnistis citrella); Pier (Pieris spp.), small cabbage moth (Plutella xylostella), prodenia litura belongs to (Prodenia spp.); Pseudo-stone roller Noctua (Pseudaletia spp.), soybean chi noctuid (Pseudoplusia includens), Pyrausta nubilalis (Hubern). (Pyrausta nubilalis); Greedy Noctua (Spodoptera spp.), Thermesia gemmatalis, bag rain moth (Tinea pellionella); Curtain rain moth (Tineola bisselliella), the green volume of oak moth (Tortrix viridana), powder Noctua (Trichoplusia spp.);
Orthoptera (Orthoptera), for example, residential house Chinese mugwort Xi (Acheta domesticus); Oriental cockroach (Blatta orientalis), Groton bug (Blattella germanica), Gryllotalpa spp (Gryllotalpa spp.); Leucophaea maderae (Leucophaea maderae), migratory locusts belong to (Locusta spp.), and black locust belongs to (Melanoplus spp.); Periplaneta americana (Periplaneta americana), desert locust (Schistocerca gregaria);
Thysanoptera (Thysanoptera), for example, rice thrips (Baliothrips biformis); Enneothrips flavens, flower thrips belongs to (Frankliniella spp.), Heliothis (Heliothrips spp.); Greenhouse Hercinothrips spp (Hercinothrips femoralis); Card Thrips (Kakothrips spp.), grape thrips (Rhipiphorothrips cruentatus), hard Thrips (Scirtothrips spp.); Taeniothrips cardamoni, Thrips (Thrips spp.);
Protozoon guiding principle (Protozoa) for example, eimeria (Eimeria spp.);
Gutstring worm (Ascaridina (Ascaridida)), for example Ascaris (Ascaris spp.) is like Ascaris lumbricoides (Ascaris lumbricoides), Ascaris suum; Ascaridia galli, Parascaris equorum, pinworm (Enterobius vermicularis) (pinworm); Toxocara canis; Toxascaris leonine, Skrjabinema (Skrjabinema spp.) and Oxyuris equi;
Camallanida (Camallanida), for example Dracunculus medinensis (guinea worm)
Spirurata (Spirurida), for example Thelazia (Thelazia spp.) Wu Ce belongs to (Wuchereria spp.) like wuchereria bancrofti (Wuchereria bancrofti), and the cloth Shandong belongs to (Brugia spp.) like cloth Shandong, Malaysia nematode (Brugia malayi); Brugia timori,, Onchocerca (Onchocerca spp.); Dirofilari spp.; Bivalve Filaria (Dipetalonema spp.), setaria (Setaria spp.), velvet Eimeria (Elaeophora spp.); Spirocerca lupi, and Ostertagia (Habronema spp.);
Tool tartar worm (Acanthocephala (Acanthocephala)), Acanthocephalus (Acanthocephalus spp.) for example, Macracanthorhynchus hirudinaceus and knot occupy Acanthocephalus (Oncicola spp);
Planaria (platyhelminth class (Plathelminthes)):
Fluke (Trematoda (Trematoda)); Faciola spp. for example; Fascioloides magna, Paragonimus (Paragonimus spp.), Dicrocoelium (Dicrocoelium spp.); Fasciolopsis buski, Clon (Clonorchis spp.) is like Clonorchis sinensis; Schistosoma (Schistosoma spp.), Trichobilharzia spp., Alaria alata, Paragonimus (Paragonimus spp.) and Nanocyetes spp;
Cercomeromorpha, particularly Eucestoda (Cestoda) (tapeworm), for example Diphyllobothrium (Diphyllobothrium spp.); Tenia spp., Echinococcus (Echinococcus spp.), Dipylidium caninum; Multiceps (Multiceps spp.), Hymenolepis (Hymenolepis spp.), Mesocestoides (Mesocestoides spp.); Vampirolepis spp., Moniezia (Moniezia spp.), Anaplocephala (Anoplocephala spp.); Sirometra spp., Anaplocephala (Anoplocephala spp.), and Hymenolepis (Hymenolepis spp).
Formula I compound is prevented and kill off Diptera (Diptera), Siphonaptera (Siphonaptera) and Ixodida insect with the compsn that contains them particularly usefully.
In addition, to be used to resist the purposes of mosquito be preferred especially for formula I compound and the compsn that contains them.
Formula I compound is of the present invention preferred embodiment another with the purposes of the compsn antagonism fly that contains them.
In addition, formula I compound is preferred especially with the purposes of the compsn antagonism Siphonaptera that contains them.
Formula I compound is an another preferred implementation of the present invention with the purposes of the compsn antagonism tick that contains them.
Formula I compound resists entozoa (including but not limited to nematode, tapeworm, fluke and protozoon) also particularly usefully.
Formula I compound can be through contact (via soil, glass, wall, tester, carpet, felt rug or animal part) and (for example bait) onset of ingesting.
The present invention relates to formula I compound prevents and kill off and/or resists in the animal body and/or ectozoal treatment and non-therepic use.
Can be through contacting with the formula I compound that kills parasitic significant quantity, formula I compound is used for watching for animals to be avoided parasite and attacks or infect.At this point; " contact " comprises that direct contact (is applied directly over said compound on the parasite; For example also its location and randomly also said compound is directly given on animal) and indirect contact (said compound is applied to the parasite location).To come the contact parasitic thing be the instance of formula I compound non-therapeutic purposes through being applied to its location.
" location " as above defines and means beyond the animal habitat, food supply, breeding farm, zone, material or the environment that parasite are wherein being grown and maybe can grown.Compound of the present invention can also prophylactically be applied to expection and have insect or parasitic place.
Can carry out with processing ground to using of animal with preventing.Using of active compound directly carried out or carried out with suitable formulations form per os, part/skin or stomach other places.
To warm-blooded animal, formula I compound can be formulated as animal-feed, animal feed premix thing for Orally administered, the animal-feed enriched material, and pill, solution, paste, suspension-s, filling is taken medicine, gel, tablet comprises chewable tablets, pill and capsule.In addition, formula I compound can give to animal in tap water.For Orally administered, the formulation of selection should provide 0.01mg/kg to the 100mg/kg the weight of animals formula I compound of every day to animal, preferably the formula I compound of 0.5mg/kg to 100mg/kg the weight of animals every day.
Alternatively, formula I compound can give animal in the stomach other places, for example through in the cud, intramuscular, intravenously or subcutaneous injection.Formula I compound can be scattered in or be dissolved in the physiology acceptable carrier, is used for subcutaneous injection.Alternatively, formula I compound can be mixed with the implant that is used for subcutaneous administration.In addition, formula I compound can transdermal administration to animal.For parenteral administration, the formulation of selection should provide 0.01mg/kg to the 100mg/kg the weight of animals formula I compound of every day to animal.
Formula I compound can also be with drops, pulvis, and powder, necklace, medallion, sprays, shampoo, basting agent, spraying and bold and vigorous form topical application of watering agent preparaton and ointment or oil-in-water or water-in-oil emulsion are to animal.For topical application, drops and sprays comprise 0.5ppm to 5 usually, 000ppm and preferred 1ppm to 3, the formula I compound of 000ppm.In addition, formula I compound can be formulated as animal, particularly the ear tag of tetrapods such as ox and sheep.
Sprinkle and to water the agent preparaton and be described in U.S. Patent number 6,010,710, incorporate it into this paper by reference at this.Sprinkle and water advantageously butyrous of agent preparaton, and generally comprise thinner or vehicle, also comprise the solvent (for example organic solvent) of activeconstituents if the latter is insoluble in thinner.
The basting agent preparaton is described in U.S. Patent number 6,395,765; 6,867,2296,096,329; 6,426,333 and 6,685,954, all incorporate its disclosure into this paper by reference at this.
Suitable preparation includes, without being limited to:
-solution such as oral liquid, the enriched material of orally give is used on the skin or endoceliac solution after the dilution, pouring preparaton, gel;
-be used for the emulsion and the suspension-s of oral or dermal administration; Semi-solid preparation;
-preparaton, wherein active compound is treated to ointment base or is oil-in-water or water-in-oil emulsion matrix;
-solid preparation such as powder, pre-composition or enriched material, granule, pelleting agent, tablet, pill, capsule; Aerosol and inhalation and contain the formed article of active compound.
The compsn that is suitable for injecting is through being dissolved in activeconstituents in The suitable solvent or the carrier, and optional other composition that adds prepares like acid, alkali, buffer reagent salt, preserving agent and solubilizing agent.Can solution be filtered and aseptic filling.The suitable solvent is the sufferable solvent of physiology, comprises alkanol such as ethanol, butanols, Virahol, phenylcarbinol, glycerine, Ucar 35, polyoxyethylene glycol, N-methyl-pyrrolidone, 2-Pyrrolidone and composition thereof like water and organic solvent.Other The suitable solvent includes but not limited to, acetyl tributyl citrate, fatty acid ester such as lipid acid dimethyl ester, diisobutyl adipic acid ester, acetone; Acetonitrile, butyldiglycol, N,N-DIMETHYLACETAMIDE, N, dipropylene glycol n-butyl ether; 1 list ether, the 1 monomethyl ether; The monomethyl ethanamide, dipropylene glycol monomethyl ether, liquid polyoxy 1; Diethylene glycol monoethyl ether, 1 and diethyl phthalate, or at least two kinds mixture in these solvents.
Active compound can randomly be dissolved in sufferable vegetables oil that is suitable for injecting of physiology or synthetic oil.
Can mention vegetables oil as vehicle or thinner, such as but not limited to VT 18, peanut oil, Viscotrol C, Semen Maydis oil, levant cotton oil, sweet oil, rapeseed oil, Trisun Oil R 80, coconut wet goods; MO, such as but not limited to, Vaseline, paraffin, silicone etc.; Aliphatic series or cyclic hydrocarbon, or alternatively for example medium chain (like C
8-C
12) triglyceride level.
Suitable solubilizing agent is to promote that active compound is dissolved in primary solvent or prevents its sedimentary solvent.Instance is a Vinylpyrrolidone polymer, Z 150PH, polyoxyethylene alkylphenol Viscotrol C and polyoxyethylene alkylphenol SPAN.Suitable preserving agent is a phenylcarbinol, Trichloroisobutyl Alcohol, p-hydroxybenzoate class and n-butanols.
In some embodiment of topical composition, said compsn can be promptly uses the solution form, like the for example description of U.S. Patent number 6,395,765, incorporates it into this paper by reference.Outside the active agent compound, promptly can comprise crystallization inhibitor, organic solvent and organic cosolvent with solution.
In some embodiments, crystallization inhibitor can exist with about 1 to about 30% (w/v) ratio.Typically, crystallization inhibitor can exist with about 1% to about 20% (w/v) or about 5% to about 15% (w/v) ratio.Acceptable suppressor factor is when using preparaton, to add preparaton to suppress crystal formation those.In some embodiments, preparaton can comprise and is different from listed those the compound that serves as crystallization inhibitor of this paper.In these embodiments; The suitability of crystallization inhibitor can by test its whether fully the crystal formation test of inhibition confirm: 20 ℃ place on the glass slide through 24 hours situation under; The sample that in aforesaid solvent, contains 10% (w/v) formula I compound has under the situation of 10% (w/v) crystallization inhibitor and is causing less than 20, preferably is less than 10 crystal.
Being used for crystallization inhibitor of the present invention includes but not limited to:
(a) Vinylpyrrolidone polymer, polyvinyl alcohol, the multipolymer of vinyl-acetic ester and vinylpyrrolidone copolymers, 2-Pyrrolidone comprises N-Methyl pyrrolidone; Methyl-sulphoxide, polyoxyethylene glycol, phenylcarbinol; N.F,USP MANNITOL, glycerine, the T 46155 ester class of sorbyl alcohol or anhydro sorbitol; Yelkin TTS or carmethose; Or acrylic acid derivative, like the polymkeric substance of methacrylic ester and derived from propylene acid mono, like inhibition active agent crystalline solvent described herein, or the like;
(b) aniorfic surfactant is like alkaline stearate (for example StNa, potassium or ammonium salt); Calcium stearate or triethanolamine stearate; Sodium abietate; Alkyl-sulphate, it includes but not limited to Sodium Lauryl Sulphate BP/USP and hexadecyl sodium sulfate; X 2073 or dioctyl sodium sulphosuccinate; Or lipid acid (for example Oleum Cocois);
(c) cationic surfactant is like water miscible formula N
+R ' R " R ' " R " " Y
-Quaternary ammonium salt, wherein the R residue is equal to or the hydrocarbon residue of different optional hydroxylation and Y
-Be the negatively charged ion of strong acid, like the halogen negatively charged ion, sulfate radical and azochlorosulfonate acid anion; The hexadecyl trimethylammonium bromide is one of spendable cationic surfactant;
(d) formula NR ' R " R ' " amine salt, wherein the R residue is to be equal to or the hydrocarbon residue of different optional hydroxylation; Octadecane amine salt acidulants is one of operable cationic surfactant;
(e) non-ionics is like the ester class of the randomly T 46155ization of anhydro sorbitol, the alkyl ether of for example Polysorbate 80, or T 46155ization; The polyoxyethylene glycol stearate, the verivate of the T 46155ization of Viscotrol C gathers sweet alkoxide, the Fatty Alcohol(C12-C14 and C12-C18) of T 46155ization, the multipolymer of the lipid acid of T 46155ization or the multipolymer of oxyethane and propylene oxide;
(f) amphoterics is as through substituted lauryl betaine compound; Perhaps
(g) list in above-mentioned (a)-(f) said compound at least two kinds mixture.
Oral liquid directly gives.Enriched material is orally give after being diluted to working concentration in advance.Oral liquid and enriched material are according to prior art and as above prepare injection liquid is said, and sterile procedure is optional.
In one embodiment of the invention, said compsn can be a paste form.The instance of paste form embodiment includes but not limited to be described in U.S. Patent number 6,787, and 342 and 7,001, those of 889 (incorporating this paper separately by reference into).
Being used for solution on the skin can drop down and drip, apply, rub, spray or spray.
Be used on the skin solution according to prior art and according to preceding text to the description of injection liquid preparation, sterile procedure is optional.
Other The suitable solvent comprises W 166, phenylethyl alcohol, phenoxyethyl alcohol, ester such as acetate ethyl ester or acetate butyl ester, peruscabin; Ethers such as alkane glycol alkyl ether, DPGME for example, ketone such as acetone, methyl ethyl ketone; Aromatic hydrocarbon, vegetables and synthetic oil, N, N,N-DIMETHYLACETAMIDE; Transcutol, solketal, Texacar PC, and composition thereof.
Can advantageously during preparation add thickening material.Suitable thickening material comprises inorganic thickening material such as bentonite, colloid silicic acid, aluminum monostearate, organic thickening agent such as derivatived cellulose, polyvinyl alcohol and multipolymer thereof, propenoate and methacrylic ester.
Gel is administered to or sprawls on skin or introduces in the body cavity.Gel prepares like this: will handle the transparent material of type of obtaining ointment quality like preceding text with enough thickening materials to the solution of the description preparation of injection liquid.The thickening material that adopts comprises above-mentioned thickening material.
Sprinkle and water the restricted areas that the agent preparaton was poured onto or was sprayed to skin, thus an active compound transdermal and a general action.
Sprinkle water the agent preparaton can be through making active compound dissolving, anti-sedimentation or be emulsifiable in suitable skin compatibility solvent or solvent mixture prepares.If suitably, add other auxiliary agent such as tinting material, bio-absorbable promotes material, inhibitor, photostabilizer, tackiness agent.
The suitable solvent, it comprises water, alkanol, glycols, polyoxyethylene glycol; W 166, glycerine, aromatic alcohols such as phenylcarbinol, phenylethyl alcohol, Phenoxyethanol; Ester class such as ETHYLE ACETATE, acetate butyl ester, peruscabin, ethers such as aklylene glycol alkyl ether such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether; Ketone such as acetone, methyl ethyl ketone, cyclic carbonate salt such as Texacar PC, ethylene carbonate, aromatics and/or aliphatic hydrocrbon; Plant or synthetic oil, DMF, N,N-DIMETHYLACETAMIDE, n-alkyl pyrrolidone such as SL 1332, n-butylpyrrolioine ketone or n-octyl pyrrolidone; N-Methyl pyrrolidone, 2-Pyrrolidone, 2,2-dimethyl--4-oxygen base-methylene radical-1,3-dioxolane and glycerol formal.
Suitable tinting material comprises and allows all coloring agent that is used for animal and can dissolves or suspend.
Suitable absorption promotes that material comprises, DMSO for example, film-spreading oil solution such as tetradecanoic acid isopropyl esters, the dipropylene glycol pelargonic esternonate, silicone oil and with the multipolymer of polyethers, fatty acid ester, triglyceride level, Fatty Alcohol(C12-C14 and C12-C18).
Suitable inhibitor comprises sulphite or metabisulfite such as pyrosulphite hydrogen potassium, xitix, butylhydroxy toluene, butylated hydroxy anisole, and Viteolin.
Suitable photostabilizer comprises, for example, and novantisolic acid.
Suitable tackiness agent comprises, for example, and derivatived cellulose, starch derivative, polyacrylic, natural polymer such as alginate, gelatin.
Emulsion can be oral, skin or give parenterally.Emulsion is water-in-oil type or oil-in-water type.They can prepare like this: active compound is dissolved in hydrophobic phase or aqueous favoring; And by examples of suitable emulsifiers with itself and other solvent homogenize mutually, if suitably with other auxiliary agent such as tinting material, absorb and promote material, preserving agent, inhibitor, photostabilizer, the homogenize of tackify thing.
The suitable hydrophobic Liquid Paraffin that comprises mutually, silicone oil, crude vegetal such as til, Prunus amygdalus oil, Viscotrol C, synthetic glycerine three esters are like two caprylics/last of the ten Heavenly stems ester, with chain length C
8-C
12Vegetable fatty acid or other are selected the triglyceride mixture of natural acid specially, possibly also contain the partial glyceride mixture of the saturated or unsaturated fatty acids of oh group, C
8-C
10The direactive glyceride of lipid acid and two glyceryl ester, fatty acid ester such as Triple Pressed Stearic Acid ethyl ester, two-n-butyryl radicals adipic acid ester, lauric acid hexyl ester, n-nonanoic acid dipropylene glycol ester, the lipid acid of medium chain branching and chain length C
16-C
18The ester of saturated fatty alcohol, Isopropyl myristate, palmitinic acid isopropyl esters, chain length C
12-C
18The suffering of saturated fatty alcohol/decylate class, Triple Pressed Stearic Acid isopropyl esters, oleic oil alkenyl esters, oleic acid decyl ester; OE, lactic acid ethyl ester, wax fatty acid ester such as synthetic duck uropygial gland fat, phthalic acid dibutyl ester; The hexanodioic acid diisopropyl ester, with the ester mixture relevant with the latter, Fatty Alcohol(C12-C14 and C12-C18) such as oneself three decyls alcohol, 2-Standamul G; The hexadecyl VLTN 6, oleyl alcohol and lipid acid such as oleic acid and composition thereof.
Suitable aqueous favoring is: water, alcohols such as Ucar 35, glycerine, sorbyl alcohol and composition thereof.
Examples of suitable emulsifiers comprises non-ionics, GREMAPHOR GS32 for example, polyethoxylated polyoxyethylene-sorbitan mono-oleate; Arlacel-60; Glyceryl monostearate, polyoxy ethyl stearate, alkyl phenol polyethylene glycol ethers; Amphoterics such as N-lauryl-p-imino-diacetic propionic acid disodium salt or Yelkin TTS; Aniorfic surfactant, like Sodium Lauryl Sulphate BP/USP, fatty alcohol ether sulphate, one/dialkyl group polyethylene glycol ether phosphate monoethanolamine salt; With the cation activity tensio-active agent, like chlorination hexadecyl trimethyl ammonium.
Other suitable auxiliary agent is: strengthen the material of emulsion viscosity and stabilized emulsion, and like Cellulose,ether with glycolic acid, methylcellulose gum and other Mierocrystalline cellulose and starch derivative, polyacrylic; Alginate, gelatin, Sudan Gum-arabic; Vinylpyrrolidone polymer, Z 150PH, the multipolymer of ethylene methacrylic ether and maleic anhydride; Polyoxyethylene glycol, wax, the mixture of colloid silicic acid or above-mentioned substance.
Suspension-s can orally give or partly/gives skin.They can prepare like this: the active compound that in suspending agent, suspends, if suitably would add other auxiliary agent such as wetting agent, tinting material, bio-absorbable promotes material, preserving agent, inhibitor, photostabilizer.
The liquid suspending agent comprises whole homogeneous solvents and solvent mixture.
Suitable wetting agent (dispersion agent) comprises above-mentioned emulsifying agent.
Other auxiliary agent that can mention comprises above-mentioned those.
Semi-solid preparation can orally give or partly/gives skin.They are different from above-mentioned suspension-s and the emulsion part only is their viscosity higher.
In order to prepare solid preparation,,, and make it to form desirable form if suitably then add auxiliary agent with active compound and suitable mixed with excipients.
Suitable vehicle comprises the sufferable solid, inert material of whole physiology.Used those are inorganics and organism.Inorganics is a sodium-chlor for example, carbonate such as lime carbonate, supercarbonate, aluminum oxide, titanium oxide, silicic acid, clayey soil, depositing silicon or colloid silicon, or phosphoric acid salt.Organic substance for example is, sugar, Mierocrystalline cellulose, food and feed such as milk powder, animal powder, flour and paddy bits, starch.
Suitable auxiliary agent comprises the preserving agent that preceding text have been mentioned, inhibitor, and/or tinting material.
Other suitable auxiliary agent comprises lubricant and glidant such as Magnesium Stearate, Triple Pressed Stearic Acid, talcum powder; Bentonite, disintegration promotion property material such as starch or crosslinked Vinylpyrrolidone polymer, tackiness agent such as starch; Gelatin or linear polyethylene pyrrolidone and do not have aqueous adhesive such as Microcrystalline Cellulose.
Generally speaking, " parasiticide significant quantity " means the amount that growth is realized the needed activeconstituents of observable effects, comprises necrosis, death, and retardance prevents and removes, and destroys, and perhaps reduces the target organisms body and exists and its active effect.For the used all cpds/compsn of the present invention, the parasiticide significant quantity can change.The said compsn of parasiticide significant quantity also changes according to the parasiticide effect of underlying condition such as hope and time length, target kind, mode of administration etc.
Can be used for compsn of the present invention comprise can generally about 0.001 to 95% formula I compound.
In some embodiments, advantageously with 0.5mg/kg to 100mg/kg every day, the total amount of preferred 1mg/kg to 50mg/kg every day is used formula I compound.
What contain said compound promptly uses preparation with 10ppm to 80% weight, preferred 0.1 to 65% weight, and more preferably 1 to 50% weight, most preferably the concentration of 5 to 40% weight works to the preferred epizoa of parasite.
The preparation of dilution typically contains the ectozoic compound of antagonism before using, and its concentration is 0.5 to 90% weight, preferred 1 to 50% weight.
In addition, preparation typically comprises the entozoal formula I compound of antagonism, and its concentration is 10ppm to 2% weight, preferred 0.05 to 0.9% weight, preferred very especially 0.005 to 0.25% weight.
The significant quantity of epizoon agent can be selected from about 0.1mg/kg to about 200mg/kg animal weight or about 1 scope to about 200mg/kg animal weight in killing in the preparation.
The veterinary compositions that comprises The compounds of this invention can randomly also comprise at least a other relevant parasiticide composition, like insecticide, miticide, parasiticide etc.
Other parasiticide can be epizoon agent in the killing of macrolide type.This macrolide type parasiticide includes but not limited to Avermectins (avermectins) and verivate thereof, and it includes but not limited to Avrmectin (abamectin), Dimasdectin (dimadectin); Doramectin (doramectin); Emaricin (emamectin), Eprinomectin (eprinomectin), ivermectin (ivermectin); Draw for fourth to be restrained (latidectin); Lepimectin, selamectin (selamectin), and milbemycin (milbemycin) and verivate thereof include but not limited to more visit rhzomorph (milbemectin); Moxidectin (moxidectin), nemadectin (nemadectin) and milbemycin (milbemycin) D.
The compound of Avrmectin (avermectin) and milbemycin (milbemycin) series is entozoa and the ectozoic effective wormer and the antiparasitic agents of antagonism wide region.Belonging to this serial compound is natural product or its semisynthetic verivate.The structure of these two series of compounds is closely related, and they include complicated 16-membered macrolide ring; Yet milbemycin (milbemycin) does not contain the aglucon substituting group of lactonic ring 13-position.Natural product Avermectins (avermectins) is disclosed in people's such as Albers-Schonberg USP 4,310,519, and 22,23-dihydro avermectin (avermectin) compound is disclosed in people's such as Chabala USP 4,199,569.For the general discussion (comprising the discussion of their purposes in the human and animal) of Avermectins (avermectins) referring to " Ivermectin and Abamectin, " W.C.Campbell, ed., Springer-Verlag, New York (1989).Natural milbemycin class (milbemycins) is described in people's such as Aoki USP 3; 950,360 and " The Merck Index " 12th ed., S.Budavari; Ed.; Merck & Co., Inc.Whitehouse Station, the various reference of quoting among the New Jersey (1996).The semi-synthetic verivate of these compounds is well known in the art, and for example is described in USP 5,077,308, USP 4,859,657, USP 4,963; 582, USP 4,855,317, USP 4,871,719, USP 4; 874,749, USP 4,427,663, USP 4,310,519; USP 4,199,569, USP 5,055,596, USP 4,973; 711, USP 4,978,677 and USP 4,920,148, all incorporate their full contents into this paper by reference.Preferred especially compound comprises ivermectin (ivermectin); Emaricin (emamectin); Avrmectin (abamectin), doramectin (doramectin), emaricin (emamectin); Eprinomectin (eprinomectin), moxidectin (moxidectin) and selamectin (selamectin).
Other compounds that can be included in preparaton of the present invention or the method is insect growth regulator(IGR) (IGR).The compound that belongs to this group is that the practitioner knows, and represents the different chemical classes of wide region.These compounds all come onset through growth or the growth of interference insect insect.Have ovum extremely and/or kill the compound of larva effect known to various ectozoic mezzanine levels from for example U.S. Patent number 5,439,924.Especially mention that in described these compounds growing through blocking-up mezzanine level (ovum and larva) is the adult stage, perhaps through suppressing those I GR compounds of the synthetic onset of chitin.Insect growth regulator(IGR) for example is described in USP 3,748,356; USP 3,818,047; USP 4,225,598; USP 4,798,837; With USP 4,751,225, and EP 179,022 or U.K.2, in 140,010, all incorporate its whole disclosures into this paper by reference.Through quoting the FRP A-2 that incorporates this paper into; 713; 889 have usually described the IGR combination; This combination comprises the compound and the chitin synthesis inhibitors of at least a tool juvenile hormone activity, and at least a particularly fluorine worm nitrile (fipronil) in three kinds of N-aryl diazole compounds, is used to prevent and kill off belong to various types of other many harmful insects.
The instance of operable IGR comprises the compound of simulating neotonin in animal doctor's preparaton of the present invention, particularly: azadirachtin-Agridyne, difenolan (diofenolan), fenoxycarb (fenoxycarb); Hydroprene (hydroprene), kinoprene (kinoprene), methoprene (methoprene), pyrrole propyl ether (pyriproxyfen); The tetrahydrochysene azadirachtin, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-(6-iodo-3-pyridyl methoxyl group) pyridine-3 (2H)-ketone, and chitin-synthetic inhibitor; Particularly: fluorine pyridine urea (chlorfluazuron), cyromazine (cyromazine), diflubenzuron (diflubenzuron); Fluazuron (fluazuron), flucycloxuron (flucycloxuron), WL 115110 (flufenoxuron); Fluorine bell urea (hexaflumuron), lufenuron (lufenuron), worm hydrazides (tebufenozide); Fluorobenzene urea (teflubenzuron) kills international name definition (The Pesticide Manual, the 10th edition of these compounds of bell urea (triflumuron) by them; 1994, Ed.Clive Tomlin, Great Britain).Chitin-synthetic inhibitor also comprises compound such as 1-(2; The 6-difluoro benzoyl)-3-(2-fluoro-4-((trifluoromethyl) phenylurea, 1-(2, the 6-difluoro benzoyl)-3-(2-fluoro-4-(1; 1; 2,2-tetrafluoro oxyethyl group) phenylurea and 1-(2, the 6-difluoro benzoyl)-3-(2-fluoro-4-trifluoromethyl) phenylurea.Fluorine uride (novaluron) also is the instance of IGR.Preferred especially IGR comprises methoprene (methoprenes); Pyrrole propyl ether (pyriproxyfens); Hydroprene (hydroprene), cyromazine (cyromazine), lufenuron (lufenuron); 1-(2, the 6-difluoro benzoyl)-3-(2-fluoro-4-(trifluoromethyl) phenylurea and fluorine uride (novaluron).
Other parasiticide as another classification compound part is to kill ectoparasite agent.Preferably, killing ectoparasite agent is arylpyrazole.The instance of suitable arylpyrazole is to be described in those of EP 295117 (USP 5232940,5547974,5608077,5714191,5916618 and 6372774), this with its all by reference integral body incorporate this paper into.Other N-aryl pyrazole compound is described in the US patent No. 4,963,575; 5,885,607; 6,083,519; 6,010,710; 6,096,329 (6,685,954); EP 0234119 and EP 0352944; The US patent No. 5,817,688; 5,922,885; 5,994,386; 6,124,339; 6,180,798 and 6,395,906 with EP 0780378; The US patent No. 6,069,157 and EP 0846686; The US patent No. 6,350,771 and EP 0948485, this with its all by reference integral body incorporate this paper into.Known N-aryl-pyrazoles has the excellent anti-insect such as the activity of Siphonaptera and tick.Fluorine worm nitrile (fipronil) is the N-aryl-pyrazoles of particular type; It effectively resists Siphonaptera and tick especially, and is the activeconstituents among Frontline
and the Frontline Plus
.
For example, in the arylpyrazole molecule, aromatic yl group is connected to the pyrazole group of pyrazoles 1-position, and aromatic yl group is through substituted phenyl group.Preferably, in substituted phenyl group, replace 2,4 and/or 6 that are positioned at benzyl ring, and said substituting group is selected from down group: C
1-C
4Alkyl, halogen, and C
1-C
4-alkylhalide group.More preferably, pyrazoles is chosen wantonly in the 3-position and is replaced by being selected from the part of organizing down: cyanic acid, nitro, halogen, ethanoyl or formyl radical; Choose wantonly in the 4-position by Z-S (O)
q-replace, wherein Z is C
1-C
4Alkyl or C
1-C
4-alkylhalide group and q are 0,1 or 2; And choose wantonly in the 5-position by amino group or through C
1-C
4Alkyl or C
1-C
4The substituted amino replacement of alkyloyl group.Most preferably, aryl pyrazole compound is 5-amino-1-[2,6-two chloro-4-(trifluoromethyl) phenyl]-4-[(trifluoromethyl) sulfinyl]-1H-pyrazoles-3-nitrile (" fluorine worm nitrile (fipronil) "), pyriprole and pyrafluprole.
In one embodiment, formula I compound of the present invention can give with formula 2 compounds combination as follows:
Wherein:
R
1Be alkyl, CN or halogen;
R
2Be S (O)
nR
3Or 4,5-dicyano imidazole-2-base or alkylhalide group;
R
3Be alkyl or alkylhalide group;
R
4Be hydrogen, halogen ,-NR
5R
6,-S (O)
mR
7,-C (O) R
7,-C (O) OR
7, alkyl, alkylhalide group ,-OR
8Or-N=C (R
9) (R
10);
R
5And R
6Represent hydrogen independently, alkyl, alkylhalide group ,-C (O) alkyl ,-S (O)
rCF
3Or carbalkoxy; Or
R
5And R
6Can form the divalent alkyl residue together, it is chosen wantonly and is interrupted by one or two divalent heteroatom;
R
7Be alkyl or alkylhalide group;
R
8Be hydrogen, alkyl or alkylhalide group;
R
9Be the hydrogen or alkyl residue;
R
10Be optional substituted aryl or optional substituted heteroaryl groups;
R
11And R
12Represent hydrogen independently of each other, halogen CN or NO
2
R
13Be halogen, alkylhalide group, halogen alkoxyl group, S (O)
qCF
3Or SF
5Group;
M, n, q and r represent independently of each other and equal 0,1 or 2 integer; With
X representes trivalent nitrogen atom or C-R
12Residue, three of said carbon atom other valence links form the part of aromatic ring.
For example also be contemplated that knot robe acid (nodulisporic acid) or knot robe acid derivative.The acid of knot robe is a compounds that is known in the industry as effective anti-endoparasitism agent and anti-ectoparasite agent with knot robe acid derivative.These compound-bases are in three kinds of structure A, B or C, and they have following structure:
Knot robe acid (compd A):
29,30-dihydro-20,30-oxa--knot robe acid (compd B):
With 31-hydroxyl-20,30-oxa--29,30,31,32-tetrahydrochysene-knot robe acid (Compound C)
These knot robe acid cpds A, B and C derive from the fermenting culture that the more piece spore belongs to (Nodulisporium sp.) MF-5954 (ATCC 74245), and the separation and the purifying of the acid of three kinds of knot robes are disclosed in US patent 5,399,582.The verivate of these compounds is described in the WO 96/29073 and the US patent No. 5,945,317; 5,962,499; 5,834,260; 6,399,796; 6,221,894; 6,136,838; 5,595,991; 5,299,582; With 5,614,546.
The present composition also comprises whole knot robe acid derivative known in the art, and said verivate comprises whole steric isomers, like above-mentioned those that describe in formerly open, by reference it is incorporated into and describes with each structural formula of hereinafter.The said substituting group of those structural formulas wherein carries out their names and definition in the The compounds of this invention of preceding text and other compound independently in directly definition thereafter.Particularly preferably be the basting agent preparaton that comprises following formula knot robe acid derivative:
Wherein
R
1Be (1) hydrogen, (2) are chosen substituted alkyl wantonly, and (3) are chosen substituted thiazolinyl wantonly; (4) optional substituted alkynyl; (5) optional substituted naphthenic base, (6) are chosen substituted cycloalkenyl group wantonly, and wherein the said substituting group on alkyl, thiazolinyl, alkynyl, naphthenic base and the cycloalkenyl group is 1 to 3 group; Said group is independently selected from (i) alkyl, (ii) X-C
1-C
6-alkyl, wherein X is O or S (O)
m, (iii) naphthenic base, (iv) hydroxyl, (v) halogen, (vi) cyanic acid, (vii) carboxyl, (viii) NY
1Y
2, Y wherein
1And Y
2Be H or alkyl independently, (ix) alkanoylamino and (x) aromatic acylamino, wherein said aroyl randomly is independently selected from R through 1 to 3
fGroup replace, (7) aryl or arylalkyl, wherein said aryl randomly are independently selected from R through 1 to 3
fGroup replace (8) perfluoroalkyl, (9) 5-or 6-unit heterocycle; It contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen-atoms; It is optional by 1 to 3 group replacement that is independently selected from hydroxyl, oxo, alkyl and halogen, and it can be saturated or part is undersaturated, R
2, R
3, and R
4Be OR independently
a, OCO
2R
b, OC (O) NR
cR
dPerhaps R
1And R
2Representative=O ,=NOR
aOr=N-NR
cR
dR
5And R
6Be H; Perhaps R
5And R
6Representative-O-together; R
7Be (1) CHO or fragment (2)
Wherein
# representes the key of connection mode I ' molecule, R
8Be (1) H, (2) OR
aOr (3) NR
cR
d, R
9Be (1) H or (2) OR
a, R
10Be (1) CN, (2) C (O) OR
b, (3) C (O) N (OR
b) R
c, (4) C (O) NR
cR
d, (5) NHC (O) OR
b, (6) NHC (O) NRCR
d, (7) CH
2OR
a, (8) CH
2OCO
2R
b, (9) CH
2OC (O) NR
cR
d, (10) C (O) NR
cNR
cR
dOr (11) C (O) NR
cSO
2R
bAnd wherein
Expression singly-bound or two key, and wherein
R
aBe (1) hydrogen, (2) are chosen substituted alkyl wantonly, and (3) are chosen substituted thiazolinyl wantonly; (4) optional substituted alkynyl, (5) are chosen substituted alkyloyl wantonly, and (6) are chosen substituted enoyl-wantonly; (7) optional substituted alkynes acyl group, (8) are chosen substituted aroyl wantonly, and (9) are chosen substituted aryl wantonly; (10) optional substituted cycloalkanes acyl group; (11) optional substituted cyclenes acyl group, (12) are chosen substituted alkane alkylsulfonyl wantonly, and (13) are chosen substituted naphthenic base wantonly; (14) optional substituted cycloalkenyl group, wherein the said substituting group on alkyl, thiazolinyl, alkynyl, alkyloyl, enoyl-, alkynes acyl group, aroyl, aryl, cycloalkanes acyl group, cyclenes acyl group, alkane alkylsulfonyl, naphthenic base and the cycloalkenyl group is 1 to 10 and is independently selected from hydroxyl, alkoxyl group, naphthenic base, alkoxy aryl, NR
gR
h, CO
2R
b, CONR
cR
dGroup with halogen; (15) perfluoroalkyl; (16) aryl sulfonyl, optional by 1 to 3 group replacement that is independently selected from alkyl, perfluoroalkyl, nitro, halogen and cyanic acid, or (17) 5-or 6-unit heterocycle; It contains 1 to 4 heteroatoms that is selected from oxygen, sulphur and nitrogen, and said heteroatoms is optional to be independently selected from alkyl, thiazolinyl, perfluoroalkyl, amino, C (O) NR by 1 to 4
cR
d, cyanic acid, CO
2R
bReplace with the group of halogen, and it can be saturated or part is undersaturated; R
bBe (1) H, (2) are chosen substituted aryl wantonly, and (3) are chosen substituted alkyl wantonly; (4) optional substituted thiazolinyl; (5) optional substituted alkynyl, (6) are chosen substituted naphthenic base wantonly, and (7) are chosen substituted cycloalkenyl group wantonly; Or (8) optional substituted heterocycle, it contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen; Wherein the said substituting group on aryl, alkyl, thiazolinyl, naphthenic base, cycloalkenyl group, heterocycle or the alkynyl is 1 to 10 and is independently selected from following group: (i) hydroxyl, (ii) alkyl, (iii) oxo, (iv) SO
2NR
gR
h, (v) alkoxy aryl, (vi) hydroxyalkyl, (vii) alkoxyl group, (viii) hydroxy alkoxy base, (ix) aminoalkoxy, (x) cyanic acid, (xi) sulfydryl, (xii) alkyl-S (O)
m, (xiii) naphthenic base is chosen wantonly and is independently selected from R by 1 to 4
eGroup replace (xiv) cycloalkenyl group, (xv) halogen, (xvi) alkyloyl oxygen base, (xvii) C (O) NR
gR
h, (xviii) CO
2R
i, (xix) formyl radical, (xx)-NR
gR
h, (xxi) 5-to 9-unit heterocycle, it can be saturated or part is undersaturated, contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen, and optionally is independently selected from R by 1 to 5
eGroup replace, (xxii) optional substituted aryl, wherein aryl substituent is 1,2-methylenedioxy group or 1 to 5 are independently selected from R
eGroup, (xxiii) optional substituted alkoxy aryl, wherein aryl substituent is 1,2-methylenedioxy group or 1 to 5 are independently selected from R
eGroup and (xxiv) perfluoroalkyl; R
cAnd R
dBe independently selected from R
bOr R
cAnd R
dThe N that is connected to them together forms 3-to 10-unit ring, and this ring contains 0 to 2 and is selected from O, S (O)
mWith the other heteroatoms of N, said heteroatoms is optional to be independently selected from R by 1 to 3
g, hydroxyl, sulfo-and oxo group replace; R
eBe (1) halogen, (2) alkyl, (3) perfluoroalkyl, (4)-S (O)
mR
i, (5) cyanic acid, (6) nitro, (7) R
10(CH
2) v-, (8) R
iCO
2(CH
2) v-, (9) R
iOCO (CH
2) v-, (10) are chosen substituted aryl wantonly, and wherein said substituting group is 1 to 3 in halogen, alkyl, alkoxyl group or the hydroxyl, (11) SO
2NR
gR
h, or (12) amino; R
fBe (1) alkyl, (2) X-C
1-C
4Alkyl, wherein X is O or S (O)
m, (3) thiazolinyl, (4) alkynyl, (5) perfluoroalkyl, (6) NY
1Y
2, Y wherein
1And Y
2Be H or alkyl independently, (7) hydroxyl, (8) halogen and (9) alkanoylamino, R
gAnd R
hBe (1) hydrogen independently, (2) alkyl, optional by hydroxyl, amino or CO
2R
iReplace, (3) aryl, optional by halogen, 1,2-methylenedioxy group, alkoxyl group, alkyl or perfluoroalkyl replace, (4) arylalkyl, wherein aryl is randomly through perfluoroalkyl or 1, and the 2-methylenedioxy group replaces; (5) carbalkoxy, (6) alkyloyl, (7) alkyloyl alkyl, (9) aryl alkyl carbonyl oxygen, (10) aminocarboxyl, (11) alkyl monosubstituted amino carbonyl, (12) dialkyl amino carbonyl; Perhaps R
gAnd R
hThe N that is connected to them forms 3-to 7-unit ring, and this ring contains 0 to 2 and is selected from O, S (O)
mWith the other heteroatoms of N, said heteroatoms is optional to be independently selected from R by 1 to 3
eReplace with the group of oxo; R
iBe (1) hydrogen, (2) perfluoroalkyl, (3) alkyl, (4) optional substituted aryl or arylalkyl, wherein aryl substituent is 1 to 3 group that is independently selected from halogen, alkyl, alkoxyl group and hydroxyl; M is 0 to 2; And v is 0 to 3; Perhaps its pharmacy acceptable salt.
Preferred embodiment, the present invention provides the preparaton that comprises formula I ' compound
Wherein
R
1Be (1) hydrogen; (2) optional substituted alkyl, (3) are chosen substituted thiazolinyl wantonly, and (4) are chosen substituted alkynyl wantonly; (5) optional substituted naphthenic base; (6) optional substituted cycloalkenyl group, wherein the said substituting group on alkyl, thiazolinyl, alkynyl, naphthenic base and the cycloalkenyl group is 1 to 3 and is independently selected from following group: (i) alkyl, (ii) X-C
1-C
6-alkyl, wherein X is O or S (O)
m, (iii) naphthenic base, (iv) hydroxyl, (v) halogen, (vi) cyanic acid, (vii) carboxyl and (viii) NY
1Y
2, Y wherein
1And Y
2Be H or alkyl independently, (7) aryl or arylalkyl, wherein said aryl randomly are independently selected from R through 1 to 3
fGroup replace; (8) perfluoroalkyl; (9) 5-or 6-unit heterocycle, it contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen-atoms, and said heteroatoms is optional to be replaced by 1 to 3 group that is independently selected from hydroxyl, oxo, alkyl and halogen; And it can be saturated or part is undersaturated, R
2, R
3, and R
4Be OR independently
a, OCO
2R
b, OC (O) NR
cR
dPerhaps R
1And R
2Representative=O ,=NOR
aOr=N-NR
cR
dR
5And R
6Are H; Perhaps R
5And R
6Representative-O-together; R
7Be (1) CHO or fragment (2)
Wherein
# representes to be connected to the key of formula I ' molecule, R
8Be (1) H, (2) OH, or (3) NH
2R
9Be (1) H or (2) OH; R
10Be (1) C (O) OR
b, (2) C (O) N (OR
b) R
c, (3) C (O) NR
cR
d, (4) NHC (O) OR
b, (5) NHC (O) NR
cR
d, (6) CH
2OR
a, (7) CH
2OCO
2R
b, (8) CH
2OC (O) NR
cR
d, (9) C (O) NR
cNR
cR
d, or (10) C (O) NR
cSO
2R
bR
aBe (1) hydrogen, (2) are alkyl randomly, and (3) are chosen substituted thiazolinyl wantonly; (4) optional substituted alkynyl; (5) optional substituted alkyloyl, (6) are chosen substituted enoyl-wantonly, and (7) are chosen substituted alkynes acyl group wantonly; (8) optional substituted aroyl; (9) optional substituted aryl, (10) are chosen substituted cycloalkanes acyl group wantonly, and (11) are chosen substituted cyclenes acyl group wantonly; (12) the optional substituted cycloalkenyl group of the optional substituted naphthenic base (14) of optional substituted alkane alkylsulfonyl (13), wherein the said substituting group on alkyl, thiazolinyl, alkynyl, alkyloyl, enoyl-, alkynes acyl group, aroyl, aryl, cycloalkanes acyl group, cyclenes acyl group, alkane alkylsulfonyl, naphthenic base and the cycloalkenyl group is 1 to 10 and is independently selected from hydroxyl, alkoxyl group, naphthenic base, alkoxy aryl, NR
gR
h, CO
2R
b, CONR
cR
dGroup with halogen; (15) perfluoroalkyl; (16) aryl sulfonyl, optional by 1 to 3 group replacement that is independently selected from alkyl, perfluoroalkyl, halogen and cyanic acid, (17) 5-or 6-unit heterocycle; It contains 1 to 4 heteroatoms that is selected from oxygen, sulphur and nitrogen, and said heteroatoms is optional to be independently selected from alkyl, thiazolinyl, perfluoroalkyl, amino, C (O) NR by 1 to 4
cR
d, cyanic acid, CO
2R
bReplace with the group of halogen, and it can be saturated or part is undersaturated; R
bBe (1) H; (2) optional substituted aryl, (3) are chosen substituted alkyl wantonly, and (4) are chosen substituted thiazolinyl wantonly; (5) optional substituted alkynyl; (6) the optional substituted cycloalkenyl group of optional substituted naphthenic base (7), or the first heterocycle of (8) optional substituted 5-to 10-, it contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen; Wherein the said substituting group on aryl, alkyl, thiazolinyl, naphthenic base, cycloalkenyl group, heterocycle or the alkynyl is 1 to 10 and is independently selected from following group: (i) hydroxyl, (ii) C
1-C
3Alkyl, (iii) oxo, (iv) SO
2NR
gR
h, (v) alkoxy aryl, (vi) hydroxyalkyl, (vii) alkoxyl group, (viii) hydroxy alkoxy base, (ix) aminoalkoxy, (x) cyanic acid, (xi) perfluoroalkyl, (xii) alkyl-S (O)
m, (xiii) naphthenic base is chosen wantonly and is independently selected from R by 1 to 4
eGroup replace (xiv) cycloalkenyl group, (xv) halogen, (xvi) alkyloyl oxygen base, (xvii) C (O) NR
gR
h, (xviii) CO
2R
i, (xix) optional substituted alkoxy aryl, wherein aryl substituent is 1,2-methylenedioxy group or 1 to 5 are independently selected from R
eGroup, (xx)-NR
gR
h, (xxi) 5 to 6-unit's heterocycles, it can be saturated or part is undersaturated, contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen, and optional is independently selected from R by 1 to 5
eGroup replace and (xxii) optional substituted aryl, wherein aryl substituent is 1,2-methylenedioxy group or 1 to 5 are independently selected from R
eGroup; R
eBe (1) halogen, (2) alkyl, (3) perfluoroalkyl, (4)-S (O)
mR
i, (5) cyanic acid, (6) amino, (7) R
iO (CH
2)
v-, (8) R
iCO
2(CH
2)
v-, (9) R
iOCO (CH
2)
v-, (10) are chosen substituted aryl wantonly, and wherein said substituting group is 1 to 3 in halogen, alkyl, alkoxyl group or the hydroxyl, or (11) SO
2NR
gR
hR
fBe (1) methyl, (2) X-C
1-C
2Alkyl, wherein X is O or S (O)
m, (3) halogen, (4) acetylamino, (5) trifluoromethyl, (6) NY
1Y
2, Y wherein
1And Y
2Be H or methyl and (7) hydroxyl independently; R
gAnd R
hBe (1) hydrogen independently, (2) alkyl, optional by hydroxyl, amino or CO
2R
iReplace, (3) aryl, optional by halogen, 1,2-methylenedioxy group, alkoxyl group, alkyl or perfluoroalkyl replace, (4) arylalkyl, wherein aryl is randomly through perfluoroalkyl or 1, and the 2-methylenedioxy group replaces; (5) carbalkoxy, (6) alkyloyl, (7) alkyloyl alkyl, (9) aryl alkyl carbonyl oxygen, (10) aminocarboxyl, (11) alkyl monosubstituted amino carbonyl, (12) dialkyl amino carbonyl; Perhaps R
gAnd R
hThe N that is connected to them forms 5-to 6-unit ring, and it contains 0 to 2 and is selected from O, S (O)
mWith the other heteroatoms of N, choose wantonly and be independently selected from R by 1 to 3
eReplace with the group of oxo; R
iBe (1) hydrogen, (2) perfluoroalkyl, (3) alkyl, (4) are chosen substituted arylalkyl wantonly, and wherein aryl substituent is 1 to 3 group that is independently selected from halogen, alkyl, alkoxyl group and hydroxyl.
Other preferred embodiment in, the present invention provides and comprises formula I ' compound compositions
Wherein
R
1Be (1) hydrogen, (2) are chosen substituted alkyl wantonly, and (3) are chosen substituted thiazolinyl wantonly, and (4) are chosen substituted alkynyl wantonly, and wherein the said substituting group on alkyl, thiazolinyl and the alkynyl is 1 to 3 and is independently selected from following group: (i) methyl, and (ii) X-methyl, wherein X is O or S (O)
m(iii) halogen, (5) aryl or arylalkyl, wherein said aryl randomly are independently selected from R through 1 to 3
fGroup replace (6) trifluoromethyl; R
2, R
3, and R
4Be OR independently
a, OCO
2R
b, OC (O) NR
cR
dPerhaps R
1And R
2Representative=O ,=NOR
aOr=N-NR
cR
dR
5And R
6Be H; Perhaps R
5And R
6Representative-O-together; R
7Be (1) CHO or fragment (2)
Wherein
# representes to be connected to the key of formula I ' molecule; R
8Be (1) H, (2) OH, or (3) NH
2R
9Be (1) H, or (2) OH; R
10Be (1) C (O) OR
b, (2) C (O) N (OR
b) R
c, (3) C (O) NR
cR
d, (4) NHC (O) OR
b, (5) NHC (O) NR
cR
d, (6) CH
2OR
a, (7) CH
2OCO
2R
b, (8) CH
2OC (O) NR
cR
d, (9) C (O) NR
cNR
cR
d, or (10) C (O) NR
cSO
2R
bR
aBe (1) hydrogen, (2) are chosen substituted alkyl wantonly, and (3) are chosen substituted thiazolinyl wantonly; (4) optional substituted alkynyl, (5) are chosen substituted alkyloyl wantonly, and (6) are chosen substituted aroyl wantonly; (7) optional substituted cycloalkanes acyl group; (8) optional substituted cyclenes acyl group, (9) are chosen substituted alkane alkylsulfonyl wantonly, and wherein the said substituting group on alkyl, thiazolinyl, alkynyl, alkyloyl, aroyl, cycloalkanes acyl group, cyclenes acyl group and the alkane alkylsulfonyl is 1 to 5 and is independently selected from hydroxyl, alkoxyl group, alkoxy aryl, NR
gR
h, CO
2R
b, CONR
cR
dGroup with halogen; (10) trifluoromethyl; (11) aryl sulfonyl, optional by 1 to 3 group replacement that is independently selected from methyl, trifluoromethyl and halogen, (12) 5-or 6-unit heterocycle; Contain 1 to 4 heteroatoms that is selected from oxygen, sulphur and nitrogen, said heteroatoms is optional to be independently selected from methyl, trifluoromethyl, C (O) NR by 1 to 4
cR
d, CO
2R
bReplace with the group of halogen, and it can be saturated or part is undersaturated; R
bBe (1) H, (2) are chosen substituted aryl wantonly, and (3) are chosen substituted alkyl wantonly; (4) optional substituted thiazolinyl; (5) optional substituted alkynyl, (6) are chosen substituted naphthenic base wantonly, and (7) are chosen substituted cycloalkenyl group wantonly; Or the first heterocycle of (8) optional substituted 5-to 6-, it contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen; Wherein the said substituting group on aryl, alkyl, thiazolinyl, naphthenic base, cycloalkenyl group, heterocycle or the alkynyl is 1 to 10 and is independently selected from following group: (i) hydroxyl, (ii) alkyl, (iii) oxo, (iv) SO
2NR
gR
h, (v) alkoxy aryl, (vi) hydroxyalkyl, (vii) alkoxyl group, (viii) hydroxy alkoxy base, (ix) aminoalkoxy, (x) cyanic acid, (x i) alkyl-S (O)
m, (xii) naphthenic base is chosen wantonly and is independently selected from R by 1 to 4
eGroup replace (xiii) cycloalkenyl group, (xiv) halogen, (xv) alkyloyl oxygen base, (xvi) C (O) NR
gR
h, (xvii) CO
2R
i, (xvii)-NR
gR
h, (xix) 5 to 6-unit's heterocycles, it can be saturated or part is undersaturated, contains 1 to 4 heteroatoms that is independently selected from oxygen, sulphur and nitrogen, and it is chosen wantonly and is independently selected from R by 1 to 5
eGroup replace, (xx) optional substituted aryl, wherein aryl substituent is 1,2-methylenedioxy group or 1 to 5 are independently selected from R
eGroup, (xxi) optional substituted alkoxy aryl, wherein aryl substituent is 1,2-methylenedioxy group or 1 to 5 are independently selected from R
eGroup and (xxii) perfluoroalkyl; R
eBe (1) halogen, (2) alkyl, (3) perfluoroalkyl, (4)-S (O)
mR
i, (5) cyanic acid, (6) R
iO (CH
2)
v-, (7) R
iCO2 (CH
2)
v-, (8) R
10CO (CH
2)
V-, (9) are chosen substituted aryl wantonly, and wherein said substituting group is 1 to 3 in halogen, alkyl, alkoxyl group or the hydroxyl, (10) SO
2NR
gR
h, or (11) amino; R
fBe (1) methyl, (2) X-C
1-C
2Alkyl, wherein X is O or S (O)
m, (3) trifluoromethyl, (4) NY
1Y
2, Y wherein
1And Y
2Be H or methyl independently, (5) hydroxyl, (6) halogen and (7) acetylamino, R
gAnd R
hBe (1) hydrogen independently, (2) alkyl, optional by hydroxyl, amino or CO
2R
iReplace, (3) aryl, optional through halogen, 1,2-methylenedioxy group, alkoxyl group, alkyl or perfluoroalkyl replace, (4) arylalkyl, wherein aryl is randomly through perfluoroalkyl or 1, and the 2-methylenedioxy group replaces; (5) carbalkoxy, (6) alkyloyl, (7) alkyloyl alkyl, (9) aryl alkyl carbonyl oxygen, (10) aminocarboxyl, (11) alkyl monosubstituted amino carbonyl (12) dialkyl amino carbonyl; Or R
gAnd R
hThe N that is connected to them forms 5-to 6-unit ring, and it contains 0 to 2 and is selected from O, S (O)
mWith the other heteroatoms of N, choose wantonly and be independently selected from R by 1 to 3
eReplace with the group of oxo; R
iBe (1) hydrogen, (2) perfluoroalkyl, (3) alkyl, (4) optional substituted aryl or arylalkyl, wherein aryl substituent is 1 to 3 group that is independently selected from halogen, alkyl, alkoxyl group and hydroxyl; And all other variable such as preceding text are to the definition of formula I '.
Particularly preferably be most such preparaton, wherein said compsn comprises knot robe acid derivative, and it is the knot robe acid amides (nodulisporamide) of following formula: compound
Wherein
Particularly preferably be most the compsn that comprises following formula: compound
Being used for the present composition, especially preferably to tie the robe amide compound be those, wherein R
XBe t-butyl (or " knot robe acid amides ").
In another embodiment of the present invention, formula I compound can give with the formamidine compound combination.The formamidine compound includes but not limited to; Amitraz (amitraz) (Mitaban
, Pfizer; Point-Guard
, Intervet; Preventic
, Virbac; Taktic
; Intervet); Chlordimeform (chlordimeform); Fourth beetle amidine (chloromebuform), formetanate (formetanate) and amine first prestige (formparanate).Amitraz (amitraz) is formamidine acaricide/insecticide of knowing, has admitted that it can be used as Scabicide and is used to prevent and kill off tick.Referring to Plumb ' s Veterinary Drug Handbook (Fifth Edition), ed.Donald C.Plumb, Blackwell Publishing, pg.34, (2005).The characteristics of formamidines are characteristic-N=CR-NR '-parts.Amitraz (amitraz) is to exist in the compound two above-mentioned parts with other member's part of formamidine.Amitraz (amitraz) has following structure:
In one embodiment, the combination of formula I compound and one or more formulas (3) formamidine compound gives:
Wherein:
X is the integer of 0-5;
R
14Be alkyl, halogen or-OC (=O) NR
aR
b, R wherein
aAnd R
bBe hydrogen or alkyl independently;
R wherein
aAnd R
bBe hydrogen or alkyl independently;
R
15Be hydrogen or alkyl;
R
16Be hydrogen or alkyl;
R
17Be hydrogen, alkyl or
Can include but not limited to 2-acyl group-4-oxo-pyrazinyl-isoquinilone derivatives with other compounds that the combination of formula I compound gives; Like PRAZIQUANTEL BP 98 (praziquantel) or 1; 4.5 6-tetrahydrochysene-2-[2-replacement] vinyl pyrimidine class and 2-[(2-is through substituted) vinyl]-2-tetrahydroglyoxaline such as pyrantel (pyrantel) are (referring to USP 3,502; 661, add this paper by reference).
The weight ratio of formula I parasiticide and other parasiticide can be about 5/1 to about 20,000/1.
The epizoon agent can be included in sustained release and the extended release preparation in Parasiticidal compound of the present invention and relevant the killing, and microballoon for example is in granule or the implant.They can be for example through in suitable vehicle Ru Shui, oil or medium chain triglyceride with the sustained release preparation of ectoparasiticide such as fluorine worm nitrile (fipronil), and/or the sustained release preparation of epizoon agent such as ivermectin (ivermectin) mixes and obtains in killing.
In this kind sustained release preparation; Preferably dispose preparaton with discharge 5 to 100mg/kg/ days 45mg/kg/ days formula I compound for example; With 0.01 to 15mg/kg/ day ectoparasiticide fluorine worm nitrile (fipronil) for example, perhaps for example epizoon agent such as ivermectin (ivermectin) in 0.5mg/kg/ days kill.
Under this kind sustained release preparation situation, very the long duration ground dosage of handling animal preferably comprises in the killing of fluorine worm nitrile (fipronil) or 2mg/kg to 3mg/kg of formula I compound and 1 to 20mg/kg particularly ivermectin (ivermectin) of epizoon agent.
In the preferred embodiment of the present invention, comprise formula I compound compositions and carry out skin ground/use partly.
Other preferred embodiment in, fixedly subsides and adhesive strip and foil form are carried out with the moulded products that contains compound such as necklace, medallion, ear tag, health in topical application.
Generally advantageously, in three all processes with 10mg/kg to 300mg/kg, preferred 20mg/kg to 200mg/kg, most preferably the total amount of the treated the weight of animals of 25mg/kg to 160mg/kg is used the solid formulations of release type I compound.
In order to prepare moulded products, use thermoplasticity and flexiplast and elastomerics and thermoplastic elastomer.Suitable plastics and elastomerics are and formula I compound enough compatible polyvinyl resin, urethane, polyacrylic, epoxy resin, Mierocrystalline cellulose, derivatived cellulose, polymeric amide and polyester.Be used for the plastics of moulded products and the detailed bill of elastomerics and preparation procedure and be provided in for example WO 03/086075.
Provide following synthetic and biological Examples illustrating the present invention, but be not construed as limiting the invention scope with any-mode.
Embodiment
Now, through following examples further explain the present invention.
S. synthetic embodiment
S.1 synthetic (5-chloro-thieno-[2,3-d] pyrimidine-4-yl)-[(S)-1-(4-trifluoromethyl sulphur alkyl-phenyl)-ethyl]-amine (Compound C .3-S)
Step 1: Synthetic 2-methyl-propane-2-(R)--sulfinic acid [1-(4-trifluoromethyl sulphur alkyl-phenyl)-ethylidene]-acid amides (S.1)
5.44g (24.7mmol) 4-(trifluoromethylthio)-methyl phenyl ketone is dissolved in 100ml THF, adds 9.33ml (9.40g subsequently; 41.2mmol) Ti (OEt)
4Add in batches 2.50g (20.6mmol) (R)-(+)-2-methyl-2-propane sulfinyl amine.At 65 ℃ of 16h that stir the mixture.After being cooled to room temperature, removing and desolvate, ETHYLE ACETATE is added to resistates.Carefully add water.Remove by filter deposition, thoroughly wash with ETHYLE ACETATE.Discard deposition.For filtrating, layer is separated, and the waterbearing stratum is with ethyl acetate extraction 2 times.The organic layer that merges is through Na
2SO
4Drying is removed and is desolvated, and obtains about 7g coarse products.Coarse products goes up purifying at silica gel (cyclohexane/ethyl acetate), obtains about 4.9g and hopes product.
Step 2:2-methyl-propane-2-(R)--sulfinic acid [(S)-1-(4-trifluoromethyl sulphur alkyl-phenyl)-ethyl]-acid amides (S.1)
5.6g (17.3mmol) (4a) is dissolved in 60ml THF, is cooled to 0 ℃.Add the THF solution of the 1.0M three sec.-butyl Peng Qinghuanas (L-selectride) of 52ml lentamente.Continue to stir 30min in this temperature.Let mixture be warmed to room temperature, continue to stir 2h.
Step 3: (S)-1-(4-trifluoromethyl sulphur alkyl-phenyl)-ethamine (S.3)
3.50g (10.8mmol) (S.2) is dissolved in 40ml methyl alcohol, at 10 ℃ of 4N HCl solution that add 5.4ml (21.6mmol) with syringe.Remove cooling bath, under room temperature, continue to stir 2h.Remove and desolvate, add water.Solution is with dichloromethane extraction 2 times.Add Na
2CO
3-solution is adjusted to alkaline pH with the waterbearing stratum, and the waterbearing stratum is with dichloromethane extraction 3 times.Merge organic layer, through Na
2SO
4Dry.Remove and desolvate, obtain the water white oil of 2.27g.The enantiomorph ratio of (S)-enantiomorph advantage of enantiomorph analysis demonstration>99:<1.
Step 4: synthetic (5-chloro-thieno-[2,3-d] pyrimidine-4-yl)-[(S)-1-(4-trifluoromethyl alkylthio-phenyl)-ethyl]-amine (Compound C .3-S)
With 2.07g (10.1mmol) 4,4-two chloro-thieno-s-[2,3-d]-pyrimidine, 0.94g triethylamine (9.2mmol) and 155mg (0.42mmol) tetrabutylammonium iodide mix in 100ml toluene.Add 1.85g (8.4mmol) (S.3), with mixture heating up to the 15h that refluxes.Be cooled to after the room temperature, remove and desolvate, add water to resistates.The waterbearing stratum is with dichloromethane extraction 3 times.Subsequently, the organic layer of merging is with 1N HCl and water washing, through Na
2SO
4Dry.Remove and desolvate, resistates is gone up purifying at silica gel (cyclohexane/ethyl acetate), obtains the Compound C .3-S of 2.37g.
Other formula I compound of the present invention can prepare by aforesaid synthetic embodiment similarly.
C. compound embodiment
Some instance that is used for preferred compound according to the method for the invention characterizes in following table C through their physical data.
Compound embodiment characterizes through for example HPLC/mass spectrometry (HPLC/MS) or their fusing point.
Analysis mode HPLC post: RP-18 post Chromolith Speed ROD, from Merck KgaA, Germany).Elutriant: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA), 40 ℃ of ratios in 5 minutes from 5: 95 to 95: 5.
Table C:
B. biological instance effect antagonism insect
Under general condition, if in addition do not specify, most test solns preparations as follows: with active compound with the desirable concentration (volume: zero(ppm) water volume): in the mixture of acetone that is dissolved in 1: 1.Test soln is using preparation on the same day.
Test soln generally is prepared as 1000ppm, 500ppm, 300ppm, the concentration of 100ppm and 30ppm (weight/volume).
B.1 cowpea aphid (bean aphid (Aphis craccivora))
Potted plant cowpea plant is settled down spraying after writing down insect colony with about 100-150 the aphid in each stage.After 24,72 and 120 hours, estimating colony reduces.
In this test, Compound C .1, C.2, C.3, C.4, C.5 and C.6 comparing with untreated control shows above 80% mortality ratio at 300ppm.
B.2 spider mite (Spider Mite) (Tetranychus (Tetranychus spp.))
Contact/Orally active:
Potted plant vegetable lamb is settled down spraying after writing down insect colony with about 50 spider mites in each stage.After 24,72 and 120 hours, estimate colony and reduce (or increasing).
In this test, Compound C .3 shows above 80% mortality ratio at 300ppm with C.6 comparing with untreated control.
B.3 brown paddy plant hopper
Before spraying, cleaned in 24 hours and washing rice seedling.Active compound is formulated in 50: 50 acetone: water (volume: volume), add 0.1%vol/vol tensio-active agent (EL 620).With the spraying of 5ml test soln, dry air places cage with potted plant rice seedling, with 10 adult inoculations.Treated rice plant is maintained at about under the 28-29 ℃ of relative humidity with about 50-60%.After 72 hours, write down the per-cent mortality ratio.
In this test, Compound C .3 shows above 80% mortality ratio at 300ppm with C.6 comparing with untreated control.
B.4 resist the activity of Aedes aegypti
Compound is formulated among the 100%DMSO, in the microtiter plate that contains 180ul 1X Luria broth culture and 10 newborn Aedes aegypti larvas, tests.Recently confirm the effectiveness of compound mutually based on the mean motion property of larva in larva mobility and the control wells that only contains DMSO.Test reduces>80% compound to confirm the EC50 value in concentration 10ppm mobility in dose-response test.
In this test, Compound C .1, C.2, C.3, C.4, the EC50 value of demonstration<1ppm C.5 and C.6.
B.5 rat kills the activity in the epizoa model
Rat is infected with 50 ctenocephalides felis.After about twenty four hours, rat (3 every group) is carried out Local treatment with the test compounds of dosage 20mg/kg or 10mg/kg body weight.Comprise placebo (vehicle) and positive controls in each research.After handling 48 hours, comb from each rat collection flea with flea.Per-cent is renderd a service every treatment group and is used computes:
% effectiveness=100x (C-T)/C
Wherein C is the survival flea geometry of numbers MV that placebo reclaims, and T is the flea geometry of numbers MV that reclaims in each treatment group.
Compound C .3-S counts (n=2 [multiplicity]) with 89% and 71% MV minimizing flea respectively at 20mg/kg and 10mg/kg dosage.
CB. contrast biological Examples
The such grade evaluation of biological activity that following table CB.1 and CB.2 show: 0%, show that lifeless matter is active, until 100%, have entirely and prevent and kill off.Carry out bioassay as described above.
CB 1. contrast bioassays 1:
With for example be disclosed in WO 2006/047397, compound number 42 wherein) comparative example CE.1 compare The compounds of this invention with the comparative example CE.2 that is disclosed in WO2007/135029 (Compound C .2 wherein) and show unexpected astoundingly more high biological activity.
The activity of table CB.1.1 control compounds CE.1
Biological | Concentration [ppm] | Compound Embodiment C .3 active [%] | Comparative example CE.1 active [%] |
Brown paddy plant hopper | 300 | 100 | 0 |
Spider mite | 300 | 90 | n.a.* |
* E.1 Compound C has 50% activity at 500ppm
The activity of table CB.1.2 control compounds CE.2
Biological | Concentration [ppm] | Compound Embodiment C .3 active [%] | Comparative example CE.2 active [%] |
Spider mite | 300 | 90 | 50 |
CB.2 contrasts bioassay 2:
For The compounds of this invention, also (for example be disclosed in the comparative example CE.2 (Compound C .2 wherein) of WO2007/135029, S-enantiomerism physical efficiency is further showed than high biological activity with the contrast of the Stereoisomeric compounds of this area.
The activity of the different steric isomers of table CB.2.1
The activity of table CB.2.2 steric isomer control compounds CE.2
Claims (36)
1. be used to resist or prevent and kill off 4-amino-thieno-[2,3-d]-pyrimidine compound of the formula I of insect, arachnids or threadworms:
Wherein
X is selected from halogen, C
1-C
10-alkyl or C
1-C
10-alkylhalide group;
R
1Be selected from down group: hydrogen, halogen, formyl radical, C
1-C
10-alkyl, C
1-C
10-thiazolinyl, C
1-C
10Alkynyl, C
1-C
10-alkylhalide group, C
1-C
10-haloalkenyl, C
1-C
10-alkynyl halide, C
1-C
10-alkoxyl group, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
10-halogen alkoxyl group, C
1-C
10-alkylthio, C
1-C
10-alkyl halide sulfenyl, C
1-C
10-alkane sulfinyl, C
1-C
10-alkyl halide sulfinyl, C
1-C
10-alkane alkylsulfonyl, C
1-C
10-alkylhalide group-alkylsulfonyl, C
1-C
10-alkylamino, C
1-C
10-alkyl halide is amino, two (C
1-C
10-alkyl) amino, two (C
1-C
10)-alkyl halide is amino, CN ,-CR
3=NOH ,-CR
3=NOCH
3With-CR
3=NOC
2H
5
R
2Be selected from down group: hydrogen, halogen, C
1-C
10-alkyl, C
1-C
10-alkylhalide group, C
1-C
10-alkoxyl group, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
10-halogen alkoxyl group, C
1-C
10-alkylthio, C
1-C
10-alkyl halide sulfenyl, C
1-C
10-alkane sulfinyl, C
1-C
10-alkyl halide sulfinyl, C
1-C
10-alkane alkylsulfonyl, C
1-C
10-alkylhalide group-alkylsulfonyl, C
1-C
10-alkylamino, C
1-C
10-alkyl halide is amino, two (C
1-C
10-alkyl) amino and two (C
1-C
10)-alkyl halide is amino;
R
3Be selected from hydrogen, C
1-C
10-alkyl or C
1-C
10-alkylhalide group;
A is
Wherein
N is 0,1 or 2;
R
4, R
5, R
8And R
9Be selected from hydrogen independently of each other, CN, C
1-C
10-alkyl or C
1-C
10-alkylhalide group;
R
6Be selected from down group: C
1-C
10The fluorine alkylhalide group, C
2-C
10The fluorine haloalkenyl, C
2-C
10Fluorine alkynyl halide and C
3-C
7Fluorine halogen naphthenic base, the carbon atom of wherein aforementioned fluorine alkylhalide group residue can further be used C
1-C
10-alkoxyl group, C
1-C
10-halogen alkoxyl group, cyanic acid and (C=O) R
qReplace, and wherein
R
qBe selected from down group: amino, C
1-C
6-alkoxyl group, C
1-C
6-halogen alkoxyl group, C
1-C
6-alkylamino, C
1-C
6-alkyl halide is amino, two (C
1-C
6-alkyl) amino and two (C
1-C
6)-alkyl halide is amino;
R
7Be selected from down group: hydrogen, halogen, CN, C
1-C
10-alkyl, C
1-C
10-alkylhalide group, C
1-C
10-alkoxyl group, C
1-C
6-alkoxy-C
1-C
6-alkyl, C
1-C
10-halogen alkoxyl group, C
1-C
10-alkylthio and C
1-C
10-alkyl halide sulfenyl;
Perhaps its enantiomorph, diastereomer or agricultural go up or veterinarily acceptable salt.
2. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of the formula I of claim 1, wherein
A is A
2And
R
9Be selected from down group: hydrogen, C
1-C
10-alkyl or C
1-C
10-alkylhalide group.
3. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of the formula I of claim 1, wherein
A is A2;
R
8Be hydrogen; And
R
9Be C
1-C
10-alkyl or C
1-C
10-alkylhalide group.
4. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of the formula I of claim 3, wherein
A is A2;
R
8Be hydrogen;
R
9Be C
1-C
10-alkyl or C
1-C
10-alkylhalide group; With
R wherein
8And R
9The substituting group at the chiral carbon atom place that is bonded to is (S)-configuration.
5. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of the formula I of claim 1, wherein
A is A2;
R
8Be hydrogen; With
R
9Be methyl.
6. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of the formula I of claim 5, wherein
A is A2;
R
8Be hydrogen;
R
9Be methyl; With
R wherein
8And R
9The substituting group at the chiral carbon atom place that is bonded to is (S)-configuration.
7. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
7Be hydrogen.
8. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
6Be C
1-C
10-fluorine alkylhalide group.
9. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
6It is trifluoromethyl.
10. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
3Be hydrogen.
11. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
2Be selected from down group: hydrogen, halogen, C
1-C
10-alkyl and C
1-C
10-alkylhalide group.
12. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
2Be hydrogen.
13. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
1Be selected from down group: hydrogen, halogen, C
1-C
10-alkyl and C
1-C
10-alkylhalide group.
14. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
R
1Be hydrogen or chlorine.
15. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
X is a halogen.
16. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
X is a chlorine.
17. according to 4-amino-thieno-[2,3-d]-pyrimidine compound of each formula I in the aforementioned claim, wherein
N is 0.
18. agricultural or veterinary science compsn, it comprises significant quantity at least a 4-amino-thieno-[2,3-d]-pyrimidine compound and at least a an inert liq and/or solid carrier like claim 1 to 17 defined formula I in each.
19. through amino-thieno-[2 like claim 1 to 17 defined formula I in each with animal pest and significant quantity; 3-d]-pyrimidine compound, or comprise wherein at least a compound compositions and contact and resist or prevent and kill off the particularly method of insect, arachnids or threadworms of animal pest.
20. through with plant or plant-growth in wherein soil or water and significant quantity like amino-thieno-[2,3-d]-pyrimidine compound of claim 1 to 17 defined formula I in each or comprise wherein at least a compound compositions and contact and protect farm crop and growing plant to avoid animal pest particularly insect, arachnids or threadworms attack or the method that infects.
21. protective plant reproductive material particularly seed avoids the method that soil insect class and protection seedling root and shoot avoid soil and the invasion and attack of blade face insects; Comprise plant propagation material seed particularly; Before sowing and/or after vernalization with significant quantity at least a like claim 1 to 17 defined formula I in each 4-amino-thieno-[2,3-d]-pyrimidine compound or comprise wherein at least a compound compositions and contact.
22. according to the method for claim 21,4-amino-thieno-of its Chinese style I [2,3-d]-pyrimidine compound is used with the amount of the every 100kg seed of 100mg to 10kg.
23. according to the method for claim 21, plant root that is wherein obtained and shoot are able to protection.
24. contain seed just like claim 1 to 17 defined formula I compound or its agriculturally useful salt in each with the amount of the every 100kg seed of 0.1g to 10kg.
25. be used to handle, prevent and kill off, prevent or watch for animals with the method for antagonism parasite infestation or infection; Comprise per os; Partly or the stomach other places to animal use significant quantity like 4-amino-thieno-[2,3-d]-pyrimidine compound of claim 1 to 17 defined formula I in each or comprise wherein at least a compound compositions.
26. according to the method for claim 25, wherein animal is not human.
27., wherein resist Siphonaptera (Siphonaptera), the parasite of Anoplura (Phthiraptera) and acarina (Acarina) according to the method for claim 25 or 26 from Diptera (Diptera).
28., wherein resist mosquito, fly, flea and/or tick according to the method for claim 25 or 26.
29., wherein resist entozoa according to the method for claim 25 or 26.
30. according to the method for claim 29, wherein said entozoa is a threadworms, tapeworm, fluke, and protozoon.
31. according to the method for claim 25 or 26, wherein said animal is a domestic animal.
32. according to the method for claim 31, wherein said animal is cat, dog.
33. according to the method for claim 25 or 26, wherein said animal is sheep, ox, horse, pig or chicken.
34. be used to prepare the purposes that per os, part or parenteral can be used the veterinary medicine that maybe can give like defined formula I compound in each of claim 1 to 17, said medicine is used for handling, prevent and kill off, prevent or watching for animals with antagonism parasite infestation or infection.
35., saidly be used for handling, prevent and kill off, prevent or watching for animals to resist parasite infestation or infection like the purposes of defined formula I compound in each of claim 1 to 17 in the preparation medicine.
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Also Published As
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CA2769385C (en) | 2017-10-17 |
CA2769385A1 (en) | 2011-02-03 |
EP2459569A1 (en) | 2012-06-06 |
EP2459569B1 (en) | 2015-07-22 |
JP2013500985A (en) | 2013-01-10 |
AU2010278948A1 (en) | 2012-02-23 |
US9133209B2 (en) | 2015-09-15 |
US20120252667A1 (en) | 2012-10-04 |
CN102596968B (en) | 2015-05-06 |
AU2010278948B2 (en) | 2015-04-23 |
MX2012001170A (en) | 2012-07-20 |
BR112012002164A2 (en) | 2015-09-15 |
BR112012002164B1 (en) | 2021-04-20 |
WO2011014660A1 (en) | 2011-02-03 |
ES2545738T3 (en) | 2015-09-15 |
JP5834006B2 (en) | 2015-12-16 |
NZ597929A (en) | 2013-09-27 |
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